So this has been the “what’s keeping you up at night?” question for me since we kicked off 2026 back in January. How do I figure out the best way for us to continue to grow without defaulting to the “more” bucket (more ad dollars, more email sends, more webinars, etc.)?

And after taking a step back a few weeks ago to look at the big picture, I have my answer.

Sponsor: YOYABA

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Like (marketing) moths drawn to the (sexy) flame

I’m going to be honest, when I realized what our biggest constraint was, I laughed out loud because of how “simple” it was. The issue was we marketers loveee us some complexity. The really deep, sophisticated, insightful finds that help us justify our existence to the company + marketing team. The ones that have leadership saying things like, “Can you believe Jenny uncovered that huge finding for us! WHAT a great hire she was!”

Whether we like to admit it or not, we marketers love those little ego dopamine hits as those are our equivalent of hitting quota that Sales has or shipping that new product/feature that Engineering has. So we reinforce that pattern by doing more “work” that gets that type of recognition.

But the downside of it is that we FLY past some of the most obvious things staring us in the face that have the most leverage. They aren’t sexy enough. Or we simply assume that they’re working just fine already and we don’t bother to examine them closely.

So as I’ve been looking at our 2026 goal + what we can do to get there, I wanted to put everything in front of myself to understand the “global” marketing system at play. We’ve been optimizing for local maximums in LinkedIn Ads, PLG email nurture sequences, etc. ad nauseam, and while we should absolutely continue to do so, I need to optimize our global maximum. And this meant taking a step back + getting all of the obvious/”simple” data front + center.

The data

Nothing crazy here. Grabbed the following 12 datapoints from the past 2 years of data + YTD so far, then put them in “sequenced” order relative to the funnel.

• Variable marketing spend (ad spend, event costs, etc.)

• Fully loaded marketing spend (variable spend above + all marketing overhead)

• Brand impressions (Google Search Console, Profound, etc.)

• Website visits (Google Analytics)

• Demo requests (Hubspot, Salesforce, etc.)

• Meetings booked (Hubspot, Salesforce, etc.)

• Discovery attended (Hubspot, Salesforce, etc.)

• Sales qualified opportunities created (Hubspot, Salesforce, etc.)

• SQO pipeline value created (Hubspot, Salesforce, etc.)

• Late-stage opportunities (Hubspot, Salesforce, etc.)

• Closed won deals (Hubspot, Salesforce, etc.)

• New revenue generated (Hubspot, Salesforce, etc.)

Once I had all of the above, I could quickly see how our global system was performing currently, quarter over quarter, and then compared to industry benchmarks for our go-to-market motion + market we sell to.

While it’s easy to see our own quarterly trends + to think “things are maintaining or slightly deviating from normal” and be ok with that is easy to be lulled into. That’s why I like to pull in industry benchmarks to see if my “normal” is actually better, worse, or on par with what’s expected. (note: yes, every company has its own nuances and benchmarks are “averages” BUT for something like this, we’re looking for directional data, not data that should be taken as dogmatic)

Once I laid out all of that data and put in calculations for conversion rates between stages, cost pers, etc., that’s where the obviousness of the constraint I need to focus on became apparent. Here’s an example of the output using dummy data to give you a sense for how I visualized this:

The most obvious constraint

In the above example, there’s a fair bit of yellow/red for performance relative to benchmarks. When I was looking at my data here at Loxo, our “sales” funnel is pretty healthy, lots of green, so the most obvious constraint jumped out at me for two reasons:

1. It was the only “red” one, telling me I was 10%+ off industry benchmarks

2. It was the one area I haven’t put any resources toward during my 3+ years here at Loxo with real intentionality

So what is this “mysterious” yet super obvious constraint that I’m now smacking myself in the back of the head for not realizing sooner? Our visit → demo requests conversion rate.

And why do I secretly love that this is our biggest constraint right now?

1. As mentioned a moment ago, we haven’t done much of anything here in a methodical way, so we have the full range of website conversion rate optimization plays at our disposal to start running through

2. There is SO MUCH LEVERAGE at this constraint. With this being so “high” in our funnel, if we were to take the rate from 1.0% to 1.5%, that then improves every single number below it. Here’s how that would play out in an example model:

Crazy right? Going from a “small” 1% to a 1.5% conversion rate in getting visitors to go to the demo request page (50% increase overall), cascades that 50% down through the rest of the funnel.

50% more demo requests
50% more SQOs created
50% more qualified pipeline
50% more deals won
50% more revenue generated

^^ me, geeking/nerding out at the upside of this kind of opportunity.

Think about it, where else can you get this type of leverage? Certainly not from adding a couple thousand more ad dollars to a campaign or hiring a few more BDRs.

All of this because I zoomed out to look at the big picture + think from a boring systems lens instead of a “sexy” channel lens.

This is what the theory of constraints is really about. It’s finding the one constraint that, when removed, cascades improvement through the entire system. It might not be the sexiest one or the most sophisticated thing in the world, but it’s the one with the most leverage. We’re quick to be seduced by complexity because it “feels” like mastery + as mentioned earlier, any chance to flaunt those “master-level” skills, we’re quick to jump at. But real mastery is seeing the lever with the highest upside for opportunity behind it, sexy or simple.

Here's one thing I'm curious about - what's your “yellow” or “red” rate? Where’s your biggest opportunity to apply leverage toward that? If you’re like me, it may be the one you've been flying past because it doesn't feel sophisticated enough to spend time on, but is well worth digging into.

Book quote of the week

“Be a maker who makes something interesting people want. Show your craft, practice your craft, and the right people will eventually find you.”

- The Almanack of Naval Ravikant, by Eric Jorgenson

See you next Saturday,
Sam

Sales leadership stood up first + said they missed their revenue target. The team was working hard but the results weren’t there.

Then marketing leadership stood up + said they had another strong quarter. We surpassed the MQL target yet again (woohoo…).

And then nobody said a damn word.

Nobody questioned how both of those things could be true at the same time. They just moved on, acting like this was completely normal and ok.

I’ve never been able to stop thinking about that room. How weird it was to be in that room when it was “normal” to everyone else in there. Then when I made my way over to Refine Labs I finally had a place where the team agreed “nah, that’s messed up and not how businesses should operate.” I’ve watched versions of that scene play out with countless clients, peers, and board horror stories for fifteen years. All incredibly smart people with good intentions + wanting to succeed, but they were unknowingly optimizing for the wrong thing because the wrong thing was what the system rewarded.

The thought that kept creeping in

The more I learned + experienced how marketing actually works, from ecosystems to force multipliers to the way a BDR call lands completely differently when the prospect has been consuming your content for months, the more I kept having this thought that our measurement frameworks seemed to be answering a different question than the one we were (or should’ve been) asking.

Every attribution tool I’ve ever used answers things like “what did each channel do?” or “who gets credit for this deal?” This leads to budgets being dictated by local maximums within channels, not a global maximum for your GTM team.

And that’s because nobody built a tool for the person who owns this outcome. The VP of Marketing, the Head of Sales, and the CFO + CEO all need to answer a completely different question: is our system working? Where is it broken? What do we do about it?

I’ve audited 100+ funnels over my career + keep finding the same patterns over and over. That’s the beauty of pattern recognition - when you can spot the same leaks, the same misdiagnoses, the same confident optimization of the wrong thing, and the same lack of outcome. That’s why we’re left giving a very wishy-washy answer to the board when they ask which channel should get more budget to hit growth targets, meanwhile the real problem is a constraint that, when “more” is added to it, only leads to more firedrills and missed targets.

If you give a mouse a cookie…

This newsletter has been the place where I’ve been working through various ideas publicly for the past few years. Some of you have been here since the beginning + for that I’m forever grateful. (and you also probably know my love of cookies, so I couldn’t help myself with the heading for this section 🤷‍♂️)

I’ve shared my thoughts on ecosystems vs. channels, AKA the argument that force multipliers don’t exist inside individual channels, that they exist in the interplay between them.

You’ve read my thoughts on being data-driven vs. data-informed, why one of the worst things you can do is disqualify a lead simply because it’s a junior title who submitted the demo request, and how most of our “goals” aren’t really goals at all.

What I didn’t tell you is that while I was writing all of that, I was also pulling the thread that leads us here to today.

The thread was a simple question: if measurement is this broken, why hasn’t anyone fixed it? What are we missing that’s making this so hard to solve for?

Meanwhile, I was reading various books + across different genres as I have been for years. Manufacturing books from 1984, biographies of people who built things in completely different domains, economics papers, the list goes on. One thing I didn’t read much of though were marketing books. I’ve read enough of those over the years to know those rarely ever get to a meaningful depth + are typically just platitudes we already know.

One of the first “aha” moments I had came from a line in the manufacturing book for 1984 (Eliyahu Goldratt’s “The Goal”) which is a novel about a manufacturing plant + their struggles. Here’s the part that stopped me in my tracks:

“The contribution of any single person to the organization’s purpose is strongly dependent upon the performance of others.”

So I read the line again. Then I replaced “person” with [channel, campaign, team, program, etc.] and realized that’s the ecosystem + force multiplier argument I’ve been making.

The problems we think are new aren’t new. They’re the same problems we’ve always had, just dressed in different clothes.

The next thread

A few months later, I was reading The Almanack of Naval Ravikant + came across his framing of the principal-agent problem. He called it the single most fundamental problem in microeconomics, but as you’re about to see, I realized it was the answer to something else we marketers have been struggling with.

Basically, the principal is the person who owns the outcome. Then the agent is the person acting on their behalf. The underlying problem he described is that agents optimize for what the principal can measure — not for the outcome itself.

I about threw my book across the room after reading that. Was a very real moment where I felt like I finally had a justification that I wasn’t crazy for going down the Goodhart’s Law rabbithole that I’d been going down lately. He framed up the entire problem with B2B marketing measurement, but using an economic concept.

The board asks us which channel is working because that’s what they can measure. So the marketing team optimizes for cost per lead on that channel because that’s what they’re rewarded by the board for. Plus, attribution tools are built to show what each agent (i.e. each channel, campaign, person, etc.) contributed toward that. Yay for credit assignment + local optimizations!

Nobody is building for the principal in the above scenarios. The person or leadership team who owns the revenue outcome + needs to understand the system as a whole in order to see where the constraints are and what to do about them. Zero help for this person/team.

So we ultimately have things like Goodhart’s Law, the principal/agent problem, and the theory of constraints all coming together in a perfect storm here. Three very different frameworks from three very different disciplines all pointing to the exact same problem.

There’s no coincidence here. As I said earlier - same problems, just wearing different clothes. Lucky for us, we know what’s really underneath those clothes thanks to these problems already having been solved, so it’s just been a matter of time to translate that to our domain.

So I kept waiting for someone to build the tool that fills that gap. And waiting. Anddd waiting some more. But nothing ever came. Attribution tools have been evolving, but not in this direction.

So I built it instead.

What is it?

Affect is a revenue diagnostic for B2B marketers and revenue leaders. It diagnoses exactly where your funnel is breaking, benchmarks your rates against real peers in your industry, and tells you what to fix first.

You run a free audit in three minutes + it benchmarks your conversion rates. It tells you where you stand relative to your industry, GTM motion, and maturity. Then it diagnoses what’s actually wrong with your funnel - a real, specific diagnosis based on your inputs. It names the root cause, gives you a prioritized action plan, + then a library of 50+ plays with timelines and success signals that you can take to improve your numbers.

Imagine you went to the doctor with chronic stomach pains and at each visit they just told you “take more pills,” but those stomach pains never got better. You’d start to question their credibility after 2–3 visits. Meanwhile, what you’re really trying to understand is why you have those stomach pains in the first place. You don’t want the band-aid solution of taking more pills to mask the pain.

This is the cycle we marketers have been in for decades. It’s time to break it.

You’re the first to hear this

This is the first place I’m publicly announcing that Affect is live. It’s a fully functioning app (well, as fully-functioning as can be at initial release 😉) + I’m already using it myself.

It’s been fun to build this. One thing that immediately came to light for me when going about this is that I’ve managed to createe a new category. I tried to find market comps for something like this + there’s nothing out there. This has all been done historically through a combination of things like:

• Consultant audits that run anywhere from $15-30k

• Industry benchmark reports from places like Gartner + cost a couple grand

• Having an in-house or fractional marketing leader ($$$ as you know)

• Then having some type of agency or internal team member who knows how to measure performance overall (but usually ends up being someone in Finance who definitely does NOT understand marketing and leads to all of those fun ROI conversations…)

So the category “name” of revenue diagnostic, the pricing I’m starting this at, etc. - I’m genuinely curious for your thoughts + feedback. Give it a shot + let me know how you’d explain what it does to a friend or colleague. More curiously, how much value does this give you? I personally know the power of what a 1% improvement to a conversion rate can do to a funnel, but that doesn’t always translate to software purchases.

The first 50 people who sign up as paying customers are going to be given the founding member rate of $99/month for life. One flat rate per entity (AKA unlimited users/teammates) + a rate lock for life (I can’t stand those “your rate is going up at renewal!” emails).

Here’s how I’ve been thinking about pricing for those who are curious.

After the first 50 sign up, the price is going to go up. The people who get in first shape what this becomes + I want those people to be the ones who believed early enough to take the bet.

But if you’re not ready to pay yet, that’s completely ok - just run the free audit first. See what it tells you about your funnel + has you start thinking about. You can come back to it + re-run it as many times as you like as time goes on.

One final note

I’ve spent years waiting for the “right” moment to do something like this, the time when I’d have more certainty to start building. Ultimately, for permission that was never going to come from anywhere/anyone.

The thing that started as a note in my phone didn’t come from some sexy or extravagant business plan or market analysis. It came from reading various books + listening to different podcasts + feeling something click. So I pulled the thread + kept pulling, building the tool I’ve always wanted out of necessity for myself, not from some ulterior motive. Or as Naval Ravikant said, “Find the problem that feels like play to you but looks like work to everyone else. You’ll outcompete anyone doing it for the outcome because you’re doing it for the thing itself.”

This is that problem for me.

Your version of this exists somewhere. The problem that feels like play to you but looks like work to everyone else + is the thing you keep coming back to. I’m not trying to AI-pill you here, but the bar has never been lower to follow your curiosity in building something. I even mentioned this in last week’s newsletter - products aren’t going to be the moat anymore, the underlying knowledge + experience that you uniquely have is what the market is going to value the most as new entrants flock in left + right.

So have fun, be curious, and go try out Affect :)

See you next Saturday,
Sam

P.S. don’t worry, this newsletter isn’t now going to become me pitching you on Affect every send moving forward. It’s going to continue as it always has, me sharing what I’m seeing + learning while leading marketing here at Loxo, but I may also start sharing some of the things I’m seeing + learning as I work with other marketers who use Affect. Trends, insights, what is/isn’t working, etc. - all the normal stuff you’d expect from me :)

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They’ve been seeing a dip in their site traffic numbers over the past handful of months. Nothing catastrophic by any means, but definitely noticeable. They wanted to understand what was happening. I told them about the alligator effect that’s come about with the increase in AI overviews + LLM searches and the rise of dark SEO + how to understand acquisition performance through this new lens.

Later that night after letting the conversation marinate some more, I realized something that’s been nagging at me for a while + crystallized through that conversation.

No one (in their right mind) wakes up excited or wanting to migrate platforms, especially a core system of record platform. They certainly don’t want to deal with data migrations. Then there’s the whole needing to learn new workflows + training the team on a new platform. It’s all painful + expensive in terms of time + resources. The only reason anyone has done this historically is if what they’re moving to is at least 10x better than what they’re leaving.

And that’s been the unspoken rule of software for years - if you want people to switch, you need to be 10x better. The 10x bar + guarantee of future improved results is what made migrations worth the pain.

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Sponsor: HockeyStack

Imagine you have a deal sitting in your forecast that's expected to close, only for it to stall because no next step was scheduled. Or because the decision-maker stopped engaging.

These signals are often unnoticed until it’s too late. The team doesn't think anything of it when the decision-maker hasn't replied for a week or two - "they're probably just busy"

Having an agent that identifies this risk + also proposes a recovery plan (i.e. finding a new champion there + proposing how to engage them) is the natural evolution of how agents should support our efforts.

HockeyStack’s new AI Revenue Agent released this week brings use cases like this to the forefront so GTM practitioners can keep + win the pipeline they worked so hard to generate. This is the future of AI agents in GTM.

Check it out

The Times They Are A-Changin’

The barrier to entry for building software is basically gone now thanks to Claude Code, Lovable, Codex, etc. It’s never been easier to build something that works + ship it to market.

The corollary to that means maintaining a true 10x product is harder than ever before. By the time you build something that’s genuinely 10x better, someone else has already copied it + built a 7x alternative that costs half as much. Then someone else copies that + builds a 5x version that’s easier to use. Then another. And another.

I’m watching this play out everywhere. The product moat is collapsing in real-time. And with this collapse comes a race to the bottom on pricing. When product/feature differentiation becomes marginal, the next lever is almost always price.

BUT - here’s one thing I’ve noticed with the companies that are actually winning in this environment + holding their ground as commoditized versions are popping up around them left + right:

They’re shifting the focus of their 10x factor from their product to the underlying knowledge infrastructure it’s built on top of.

Playbooks
Proprietary research
Frameworks for how to actually execute + get results
The community of users + UGC content from them

In short: the type of expertise that can’t be replicated by code or copied by a competitor in a weekend.

When someone uses to their platform, yes, the product is good, but what they’re really paying + staying for is the underlying knowledge + expertise that comes with it. The guidance that comes from the employees + community of users. More impactfully, the “oh yeah, we’ve seen that scenario play out before - here’s why that’s happening + here’s what does/doesn’t work to get through it.”

THAT is the stuff that makes moving platforms worth it now.

Anyone can copy a feature product in a month. But it’s really hard to copy the knowledge + insights gained from someone who has spent years in the space gaining the type of experience you can only get from first-principles thinking + execution.

Let the market copy your dashboards + features. Let them put on your clothes + dance around trying to tell the market that they’re the same as you, just a little more affordable. Because when push comes to shove + they start to get the hard questions like “why am I not getting the results your platform claimed I’d get?”, they’ll be standing there at a loss for words, because they never learned the fundamentals or gained the underlying knowledge for what the platform is actually solving for + how to execute the proper strategy from it.

You can’t build the frameworks that show people how to get 3x better results with it.

The new 10x

Most companies are still playing the old game. They’re trying to out-engineer their way to differentiation. Ship a better feature, add a new automation, etc. It’s the 10x product game + they’re losing because the that game is over.

The companies breaking ahead right now are playing the knowledge game.

This is especially important if you’re someone building something on the side thinking you have a shot at the market. You don’t need to out-build anyone. Or even if you do, expect that others are going to quickly follow suit and that moat will be gone within a few months.

BUT, you can out-think them.

What do you know that no one else knows?
What have you seen work that competitors don’t fundamentally understand?
What frameworks have you developed that the market can’t get anywhere else?
What patterns have you noticed that, if codified + shared, would be genuinely useful?

This is the real 10x. This is the new moat.

Most of you reading this are working at a company that’s already established in the market. Over the past year you’ve probably been watching new competitors pop up every month + the same thing applies here. It’s going to become harder + harder to win by having a slightly better product. But you can continue to win by being the most trusted advisor + authority in the space - AKA the ones who actually know how to help your customers succeed in driving the results they’re after.

So instead of spending all your time thinking about how to market new features, spend it on knowledge capture. What are your customers actually doing that’s working? What’s not working? What patterns are you seeing in the market? Take that + turn it into playbooks, frameworks, training sessions, etc.

My hypothesis is that over the coming year, there’s going to be a shift that starts to take place where we do less marketing of the product and more marketing of the thinking/knowledge/experience that comes with the product.

Positioning is going to shift from “we’re the #1 product in [category]” to “we have the knowledge + expertise to help those in [category] win + we’re going to teach you how.”

The knowledge you have that makes your customers 10x better at what they’re trying to do is going to be the new 10x rule.

Product is table stakes now - anyone can build one in a weekend. The true moat is the underlying thinking + knowledge.

See you next Saturday,
Sam

A quick note from me:

Everything I just wrote about above - about how the moat has shifted from product to knowledge - I’ve been living this while building Affect over the past handful of months.

I (someone with zero coding skills) built a platform in a few months that I’m sure someone else can/will replicate in a weekend. But like I wrote about above - the code isn’t the moat, the underlying knowledge is.

Affect isn’t just software. It’s the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t. The underlying conviction that marketing’s job isn’t to hit vanity metrics - it’s to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated hitting its MQL targets while the business missed revenue. For the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. For the marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

The waitlist is open today + the product will be coming out of beta in a few weeks. It would mean a lot to have you on it 🙏

Join the waitlist

You’re sitting in a quarterly business review. Sales leadership stands up first. They missed the revenue target again. The team was working hard, but the results just weren’t there.

Then marketing leadership stands up. Another strong quarter. Surpassed the MQL target yet again.

And nobody in that room says a damn word. Nobody questions how both of those things could be true at the same time. They just move on.

I sat in that room early in my career and it’s something I’ve never been able to forget.

15 years later, I’ve done something about this. I built Affect - the platform I’ve always wished for as a marketer.

Affect is for the marketers who have sat in a room where marketing celebrated hitting its targets while the business missed revenue - and felt sick about it.
The marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself.
The marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

The waitlist is open today. It would mean a lot to have you on it 🙏

Join the waitlist

My dear future CMO,

This final letter is different.

The first four I wrote to you came from a place of having lived it - the mistakes, the lessons, + the moments where I wish someone had handed me letters like these. But this letter is written from a different vantage point as I haven’t sat in this seat. I’ve watched enough people who have been there to know what I’d want to be thinking about before I got there.

So take this one for what it is - observations from someone still on their way up, written down before the moment arrives.

The first thing that will catch you off guard is that the job is less about marketing than you think.

At every level before this one, your value was tied to your ability to understand + execute marketing. At the CMO level, what actually matters is your ability to translate marketing into language the business cares about. Things like impressions, brand lift, and keyword clusters don’t mean anything outside of your marketing team.

The table you’re sitting at now is discussing revenue, margins, market position, + advancing your competitive advantage. If you can’t make that transition fluently + quickly, you’ll have a short tenure fighting for budget + credibility instead of actually leading.

And then there’s the fun part that makes it even harder - you’re almost certainly the most misunderstood executive in the room. The CFO has their financial model + the CRO has their revenue number, two very quantitative measures with binary over/underperforming metrics. The CMO has a qualitative story about why the market sees you the way it does, what it’ll take to change that, + some hypothetical models for what the outcome could look like.

Getting the room to receive that story as strategy rather than opinion is work that never stops. You’ll educate as much as you execute. Then you’ll re-educate again in a few quarters when something is “off” and the lesson has been forgotten because it never showed up cleanly in any report. This is the job now. You need to be able to market internally just as well, if not better, than you can market externally.

A second lesson: your relationships will determine everything.

Your relationship with the CEO is the foundation your entire role is built on - more than your strategy, your team, + the quality of your work. If the CEO doesn’t understand what you’re building + why it’ll work, you’ll always be one bad quarter away from having “the conversation” that no CMO wants to have. Invest in this relationship like it’s the most important project on your list.

Then there’s a second relationship most CMOs underestimate - the one with the CFO. These two functions have historically talked past each other - marketing speaks in qualitative measures, finance speaks in quantitative measures. The CMOs who figure out how to close that gap early are the ones who end up with more budget, more trust, + more room to make the big bets. You are the person who will determine if marketing is viewed as an expense or an investment.

And for your final lesson: you’re going to make a lot of decisions in this seat. Hundreds, if not thousands, of calls across strategy, budget, people, execution, messaging, positioning, + much more. But when you + others look back on your tenure, you’ll likely be defined by only one or two of those decisions: that one big swing that really worked, and then the one bet that completely flopped. It won’t be the sum of everything you did. That’s the strange one to sit with, but it’s worth thinking about now before you get there. It will inform how seriously you treat the biggest calls + how much conviction you’re willing to bring to them.

You’ll be sitting with a lot of things alone at this level. There’s nobody above you in marketing inside the company to learn from or bounce ideas around with anymore. The peers who used to be your sounding board are now your direct reports. You’ll have to be the person in the room who says the hard thing nobody else will say - whether it’s about the strategy, the market, what’s not working, or who isn’t pulling their weight. This is a burden that is yours alone. It comes with the seat.

You’ll skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.

Ever faithfully yours,
Sam

P.S. If this helped with where you’re at now, or would have when you were at this stage, share this with someone else you know who would benefit from it.

Sponsor: YOYABA

AI agents hate your website. And they don't care about your SEO rankings.

As AI agents increasingly navigate the web and execute tasks on behalf of users, your site needs to work for machines, not just humans. Problem is, if you open LinkedIn right now, you'll see a new "AI agent strategy" every day. Most of it is clickbait fluff with zero actionable substance.

On May 7th, Oliver Kuttruff (Senior SEO Consultant at YOYABA) and Crystal Carter (Head of AI Search & SEO Communications at Wix) are breaking down what an agent-ready website actually looks like in practice:

• What WebMCP is, what it isn't, and how to pick between Declarative and Imperative API approaches

• Which strategies are production-ready today and which "hacks" you can safely ignore

• How SEO is shifting from ranking pages to enabling agent actions

If you're overwhelmed by the AI agent noise and want clarity on what's actually worth implementing, you won’t want to miss this. May 7th, 2026 from 9:30-11a EST / 2:30-4p BST.

Grab your spot

Editor’s note: This is letter 5 of 5 in a series of letters to a marketer at a major inflection point in their career - the letters I wish I had at those times. If you want to start at the beginning, here they are:
To the first-year marketer
To the first-time manager
To the first-time director
To the first-time VP

*AI disclaimer: stealing this from Ashley Lewin. It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the others in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.

Subscribe now

You’re sitting in a quarterly business review. Sales leadership stands up first. They missed the revenue target again. The team was working hard, but the results just weren’t there.

Then marketing leadership stands up. Another strong quarter. Surpassed the MQL target yet again.

And nobody in that room says a damn word. Nobody questions how both of those things could be true at the same time. They just move on.

I sat in that room early in my career and it’s something I’ve never been able to forget.

15 years later, I’ve done something about this. I built Affect - the platform I’ve always wished for as a marketer.

Affect is for the marketers who have sat in a room where marketing celebrated hitting its targets while the business missed revenue - and felt sick about it.
The marketers who want to be held accountable because they're confident enough in their work to let the math speak for itself.
The marketers who understand that clarity is earned, conviction is a choice, + being a force on the business is the only version of this job worth doing.

The waitlist is open today. It would mean a lot to have you on it 🙏

Join the waitlist

My dear first-time VP of Marketing,

Congratulations. You own the marketing department now.

But I want to be direct with you about what this actually means.

Everything that happens inside the marketing department is on you now. Missing the pipeline this quarter isn’t your demand gen manager’s fault, it’s yours. The event you hosted that fell flat isn’t your event marketer’s fault, it’s yours. The product launch that didn’t drive as many handraisers as forecasted isn’t your product marketer’s fault, it’s yours. When things work, the individuals on your team get the credit. When things don’t work, you own it, that’s on you for not driving the result.

This is what it means to actually lead a department. The VPs who struggle at this level are the ones who point their finger when things go wrong. The VPs who grow fast + make it past the 18-month mark understand early that the buck stops with them. You know exactly what your job is. Now you need to drop any semblance of an ego + get ready to take a few jabs to the mouth as these are the requirements to long-term success at this level.

The next thing to learn is how to build a departmental strategy that works.

I told you about ecosystems in a previous letter. In your first marketing role, the idea was simple: don’t measure channels in isolation. In your first manager role, it was about evaluating whether inputs were doing anything to the output. At the director level, it was about building a brand coefficient that makes everything else better.

At the VP level, ecosystems goes from being a philosophy to an operating system.

You’re now making decisions that determine how the GTM motion fits together - where to apply budget, how the teams are structured, which big bets get made, and more difficult, where cuts need to be made. Viewing performance through the lens of individual channels doesn’t work at this level. You’re juggling too many balls at once. The question for you is “how is this channel affecting everything else in our GTM ecosystem?”

A BDR team that looks expensive in isolation might actually be the mechanism that drives the majority of your PLG signups to successfully activate + adopt through their follow up. The podcast that is “unattributable” might be why your win rates have been steadily rising. You have to hold the whole system in your head + make decisions at that level.

But most VPs don’t. They optimize locally because local performance is what’s easiest to prove or defend in a board meeting. Don’t fall into this trap early.

One last thing I want to tell you is about velocity.

At this level, the decisions are the most complex they’ve ever been + the information you have will never be complete. There will always be another data point to gather, another stakeholder to align, another scenario to model, etc. And if you are always waiting until you have “that one last thing,” you’ll always be waiting.

A plan without velocity never gets off the ground. The market doesn’t wait for you to have everything you need to be comfortable. Your competitors certainly won’t be waiting for you to feel ready. You need to learn to move with what you have + be prepared to iterate as you go. Success at this level is making a series of good decisions after good decisions in rapid succession, not one perfect decision made too late.

Nobody is going to give you permission to lead + do this. That’s the job you’re expected to do. You’re the one being looked to for permission now.

Remember: you’ll skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.

Ever faithfully yours,
Sam

P.S. If this helped with where you’re at now, or would have when you were at this stage, share this with someone else you know who would benefit from it.

Editor’s note: This is letter 4 of 5 in a series of letters to a marketer at a major inflection point in their career - the letters I wish I had at those times. If you want to start at the beginning, here they are:
To the first-year marketer
To the first-time manager
To the first-time director

*AI disclaimer: stealing this from Ashley Lewin (if you haven’t subscribed to her newsletter yet, definitely do. ALSO - she just launched her own company, GrowthLine Studio if anyone is looking for some fractional marketing help).
It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the others in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.

Subscribe now

You know the feeling. The one that comes when pipeline is off. You sense it + are mentally preparing yourself for the knee-jerk reaction your leadership team is going to have when they find out. You have your theories about potential causes. Leadership has theories as well, but more urgently, are telling you to fix this now. So while you spend the next week trying to see what happened, what you actually need is someone to just tell you where the funnel is broken + what to fix first.

I’ve felt that frustration my entire career. I’ve been that marketer more times than I can count. But I’ve finally had enough of it, so I’ve been moonlighting to build the tool I always wished I had.

Affect pinpoints exactly where your funnel is broken, explains the root cause of it, and tells you how to fix it. But diagnosing the problem is only step one. Affect is built to take you all the way from knowing what’s broken to making the changes to fix it to seeing exactly when those changes will hit your top of funnel, pipeline, + revenue. For the first time, you can see your fingerprints on the outcome.

The waitlist is open today. It would mean a lot to have you on it.

→ affect.so

My dear first-time director,

Congratulations. You just got “the” title.

This one is a big step for you, so it’s going to be longer than the last two letters I sent you.

Here’s the thing about titles: they have a sneaky way of trying to become the thing you work toward instead of the continued pursuit of mastery in your craft.

John Boyd would regularly warn his mentees about this trap. His frame was simple and became known as the “to be or to do” speech. You can spend your career trying to “be” someone who gets the titles + accolades, or you can spend your career doing the actual work + making a real difference in your field.

Director is not an identity. It’s a context in which you’re enabled to do more + better work. But the day you start leading with the weight of the title is the day your work starts suffering for it.

Now, something you’re going to be asked to think deeply about at this level that you probably weren’t before: brand.

I’ll save you the “should we invest in brand or demand gen?” debate you’re going to hear in every budget meeting for the rest of your career because it’s the wrong question. Brand + demand aren’t competing. Brand is the coefficient that sits in front of everything else. The same campaign, the same budget, the same BDRs produce different results depending on whether the market knows who you are + their association with you. A strong brand can make mediocre demand gen work better than it should. A weak brand can prevent even the best demand gen work from driving results.

This is going to frustrate you because you can feel your brand’s strength and can communicate that in a meeting with leadership, but they’re going to ask for data that backs this + there’s no single datapoint that “proves” this feeling for you. Don’t let that discourage you.

When a prospect gets on a call already knowing what you do + why it matters, that’s the brand coefficient at work. When a cold email gets a reply because they’ve seen your company’s name three times in the past month, that’s it. It won’t show up cleanly in any attribution model, which is exactly why most directors never fully account for it. You should.

Another thing about this level that nobody prepares you for. Some of your calls you make at this level are going to be wrong. Budget decisions, strategic bets, people decisions - you’re going to realize later on that you got some of them wrong.

This is now a part of the job. What matters is what you do when it happens.

The instinct most people have is to defend their decision. To double down + find reasons why it still might work. Or the opposite - they let it die and place blame elsewhere for why it didn’t work. I’ve watched talented directors lose the trust of their leaders + teams because they couldn’t accept the responsibility of being wrong.

Here’s a distinction worth understanding early: a bad decision and a bad outcome aren’t the same thing. You can make the right call with the information you had + still have it not work. That’s business. Hell, that’s life. What you owe people in that situation is honesty about what happened + clarity on what changes. Learn to own that + say “but here’s what we’re doing about it.”

The directors people trust the most aren’t always right. They’re just the ones who don’t make their mistakes someone else’s problem.

You’ll skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.

Ever faithfully yours,
Sam

P.S. If this helped with where you’re at now, or would have when you were at this stage, share this with someone else you know who would benefit from it.

Editor’s note: This is letter 3 of 5 in a series of letters to a marketer at a major inflection point in their career - the letters I wish I had at those times. If you want to start at the beginning, here they are:
To the first-year marketer
To the first-time manager

*AI disclaimer: stealing this from Ashley Lewin (if you haven’t subscribed to her newsletter yet, definitely do. ALSO - she just launched her own company, GrowthLine Studio if anyone is looking for some fractional marketing help).
It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the others in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.

Sponsor: HockeyStack

For the past 2 years I’ve been asking myself the same question over + over again:
“What does an ideal GTM ecosystem journey actually look like for our ICP?”

...but I still don’t have a *clear* answer

I know the answer exists + that it’s hiding in our data. I know that if I could actually see it, I could craft our GTM execution around it instead of guessing. But every time I try to piece it together, I get stuck at the same point:

“Are BDRs more successful if they’ve seen ads first?”
“Do the order of activities impact one another?”

So we’re all sitting here with tons of unstructured data that could answer these questions, but don’t have the infrastructure to actually surface the answers we’re after…until now.

HockeyStack launched Blueprints recently + it’s the first tool I’ve seen that finally shows which activities + sequences actually happen when we WIN and what is (or isn’t) happening when we LOSE.

Check it out

Subscribe now

My dear first-time manager,

Congratulations. You just got handed something new: a budget, a direct report, or both.

This is the moment many marketers get it wrong.

The instincts that made you a good individual contributor start working against you here. You were rewarded for doing, for shipping, + for driving results on the channels you owned. Now you’re responsible for a system, and systems don’t work the same way.

The mistake I made + see most often at this stage is what I call the additive mindset. You have a budget + you want to grow pipeline, so you start asking questions like:

What if we added more ad spend? What if we hired another BDR? What if we added this channel?

Then you map out the anticipated ROI of each in isolation, add it to your expected outcomes, and present your plan.

The problem with this is that nothing in a GTM motion works as independent parts. You win deals because of how channels work together - ads that build familiarity, outbound that hits at the right moment, content that gives the prospect something to trust. Remove any one of those + the others become less effective. That’s how an ecosystem operates: a series of complex interdependent parts. Evaluate it that way, not channel by channel.

The biggest learning for you here is watching channels you used to think of as additive become force multipliers for one another. The same budget, but more output because the channels are working together rather than in isolation.

But you only get there if you’re willing to ask an honest question about everything your budget touches: is the input doing anything to the output?

Not by its own metrics or confined to how it’s doing in its isolated platform. I’m talking relative to pipeline + revenue - the numbers that actually matter. I bet you’ll find that some of your highest-performing inputs by their own local measures are doing very little for the actual global result. I’ve cut keywords we “ranked” for + channels that drove “traffic” because when I asked that question honestly, the answer was no.

You’re now a steward of the business’s resources. That means asking that question even when the answer is uncomfortable.

Now, about the person you’re managing.

Every new manager defaults to giving answers. You know the job + you’ve done the job, so telling someone what to do is faster than walking them through it. The problem is that people own what they conclude themselves - they don’t own what you give them. You can’t argue someone into a belief they didn’t reason themselves into, and the same goes for getting someone to truly understand their work. Ask the questions before you give the answers. Let them arrive at it on their own.

Lastly, your team is the most accurate reflection of your standards. What you tolerate, what you push back on, where you set the bar - all of that is what they’ll calibrate to. You let the standard slip the moment you don’t say something when you should have.

Feel it early. The standard slips faster than you think.

You’re going to skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.

Ever faithfully yours, Sam

P.S. If this helped with where you’re at now, or would have when you were at this stage, share this with someone else you know who would benefit from it.

*AI disclaimer: stealing this from Ashley Lewin (if you haven’t subscribed to her newsletter yet, definitely do. ALSO - she just launched her own company, GrowthLine Studio if anyone is looking for some fractional marketing help).
It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the others in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.

Sponsor: You/Your Company?

If you’re looking to get in front of an engaged audience of some of the savviest marketers + GTM practitioners, this is your opportunity. One opening per month to sponsor this newsletter has become available + I’m sure will claimed quick, so if the audience reading this newsletter is your ICP, this is your chance.

A few weeks ago I was talking to a VP of Marketing + they said they were exploring/in negotiations with one of the sponsors of this newsletter after learning about them here + seeing them as a product that I endorse. That’s the power of these types of partnerships done well (vs. the AI influencer dumpster fire some are experimenting with).

Simply reply back to this email if you/your company is interested or drop me a DM on LinkedIn.

Subscribe now

My dear first-year marketer,

Congratulations. You got the job.

Now let me tell you a few things I had to learn the hard way.

Early in my career I sat in a quarterly business review + watched something that hasn’t left me since.

Sales leadership stood up first. Said they had a tough quarter + missed the revenue target again. The team was working hard, but the results just weren’t there.

Then marketing leadership stood up. Another strong quarter + surpassed the MQL target yet again.

And here’s the part that stuck out to me - nobody in that room said a single thing. Nobody questioned how both of these things could be true at the same time.

Growing up an athlete, I was wired a certain way. If you do the right input consistently, you’ll get the result. If you’re not getting the result, you’re either not doing enough of the input, or it’s the wrong input relative to driving that result.

What I was watching in that conference room was the second one.

Marketing had picked an input (MQLs) that wasn’t truly connected to the result (revenue) the business needed. But because marketing was only held accountable to the MQL input, they weren’t incentivized to care what happened after those were generated.

This is Goodhart’s Law in action. When a measure becomes a target, it ceases to be a good measure. B2B marketing has been breaking this law for years.

So here’s what I want you to know from day one: leads are not the goal. Revenue is the goal. You should have confidence that the work you’re doing will impact pipeline + revenue. If it isn't, it shouldn't be on your list.

The marketers who figure this out early are the ones that sales actually trusts + the ones leadership calls on when the business has a real problem to solve. That’s a different career than the one that ends with you celebrating in a conference room while the company misses its target.

You’re also going to be handed a playbook.

Question it from day one. Don’t do it loudly (yet), but internally. Ask yourself if this reflects how buyers actually behave, or if it’s how “everyone else is doing it.” Common sense and common practice are almost never the same thing in B2B.

The marketers who figure that out early treat the playbook as a starting point, not dogma. Always use the simplest filter available: would a real buyer actually respond to this?

Last thing, and this one isn’t about marketing at all: do the work because your standard demands it.

Not so you can be seen doing it. Not to prove you were worth hiring. Not to show how “busy” you are.

The right people will notice without you having to make them notice. As John Boyd used to tell his proteges, “If you insist on getting credit for the work you do, you’ll never get far in life. Don’t confuse yourself with the idea of getting credit.”

You’re going to skin your knees on a few of these before they click. That’s ok, that’s how this works. The ones you learn the hard way will stick the longest.

Ever faithfully yours,
Sam

P.S. if this would’ve helped you early on, it’ll probably help someone you know who’s just getting started

*AI disclaimer: stealing this from Ashley Lewin (if you haven’t subscribed to her newsletter yet, definitely do. ALSO - she just launched her own company, GrowthLine Studio if anyone is looking for some fractional marketing help).
It’s important to be transparent when it comes to AI usage in marketing. You all (hopefully) trust me + let me drop into your inbox each week, and I don’t want you to think I take that for granted.
I used AI for this week’s newsletter (and the 3 that will follow in this series) to help structure the writing in a way that allows me to be shorter, more direct, + have more of a “lessons + love from someone who’s been there” dynamic to it. I’m sure you picked up on that in the writing style here. My ideas, but in a slightly different style + delivery than normal in an effort to make this series more impactful.

Sponsor: HockeyStack

For the past 2 years I’ve been asking myself the same question over + over again:
“What does an ideal GTM ecosystem journey actually look like for our ICP?”

...but I still don’t have a *clear* answer

I know the answer exists + that it’s hiding in our data. I know that if I could actually see it, I could craft our GTM execution around it instead of guessing. But every time I try to piece it together, I get stuck at the same point:

“Are BDRs more successful if they’ve seen ads first?”
“Do the order of activities impact one another?”

So we’re all sitting here with tons of unstructured data that could answer these questions, but don’t have the infrastructure to actually surface the answers we’re after…until now.

HockeyStack launched Blueprints recently + it’s the first tool I’ve seen that finally shows which activities + sequences actually happen when we WIN and what is (or isn’t) happening when we LOSE.

Check it out

Subscribe now

After hearing him covered on the Founders podcast, I ordered a copy of the biography.

Overall, I thought it was a good book. Surprisingly honest for someone who built one of the largest companies in the world. Made plenty of highlights while reading it, but the part that stayed with me the most was at the end in a list he called “Things I Believe.”

He had a concise list of just over 20 principles + beliefs that he said helped shape how he built and led over the years.

As I closed the book, that left me with the thought of what would mine say?

So what follows here is my attempt to answer that question based on where I’m at in life. Most of these aren’t novel thoughts - they’re things I’ve learned, noticed, failed at, and have had to relearn. Some you’ll recognize as topics covered in prior sends of this newsletter. Some are more internal thoughts that I haven’t shared here before.

Now, in no particular order, the list of 26 things I believe:

Subscribe now

Sponsor: You/Your Company?

If you’re looking to get in front of an engaged audience of some of the savviest marketers + GTM practitioners, this is your opportunity. One opening per month to sponsor this newsletter has become available + I’m sure will claimed quick, so if the audience reading this newsletter is your ICP, this is your chance.

A few weeks ago I was talking to a VP of Marketing + they said they were exploring/in negotiations with one of the sponsors of this newsletter after learning about them here + seeing them as a product that I endorse. That’s the power of these types of partnerships done well (vs. the AI influencer dumpster fire some are experimenting with).

Simply reply back to this email if you/your company is interested or drop me a DM on LinkedIn.

The list

1. Ecosystems, not channels. The contribution of any single person, channel, or team is inseparable from everything around it. Optimize for global, not local, maximums.

2. Most problems aren’t new problems. They’re the same problems seen before, just dressed in different clothes. The person who reads + learns from areas outside their discipline will always have an advantage over the person who only learns from their own.

3. Common sense ≠ common practice. Somewhere along the way, our intuitive understanding of how buyers actually behave when making purchase decisions (AKA non-linear, messy, multiple people involved) got buried under the accumulated weight of common practice (AKA linear funnels, sequenced campaigns, decisionmaker is also the end user).

4. Brand is a force multiplier. It changes the effectiveness of everything downstream, but it doesn’t show up in dashboards + that’s exactly why most people underinvest in it.

5. Leads are not goals. Revenue is the goal. Never confuse a leading indicator for the goal itself. Remember Goodhart’s Law: “when a measure becomes a target, it ceases to be a good measure."

6. Before giving answers, ask the questions. When someone arrives at the conclusion on their own, they’ll own it in a way that explanation never produces.

7. The work is the answer. Do it because your standard demands it, not because anyone is watching. The outcomes + any recognition of those is an output of doing this at your standard, they aren’t goals themselves.

8. To do, not to be. There's a speech John Boyd used to give his proteges: you can be somebody, or you can do something. The 2 paths rarely run together for long before you have to make a choice. You can be someone + get the title, or you can do the work that makes a difference.

9. The greatest competitive advantage available right now is quality and execution. AI makes low-quality content infinite + genuine craft rarer, so it stands out.

10. Data tells you what happened, but rarely tells you why. The person who triangulates data + uses pattern recognition will always outperform the one who only trusts the dashboard.

11. Move before you have every answer. The next step reveals what the preparation couldn’t. One thing I’ve learned over the years is that knowing your direction means NOTHING without VELOCITY behind it. Velocity is the action. It’s taking the first step + making progress toward the plan we created.

12. Teams are the most accurate reflection of your standards. Hire slowly, develop relentlessly, + never tolerate what you wouldn’t do yourself.

13. Prepare before you need to. Don’t get on the field already winded. The time to build the capability is before we need to use it, not during.

14. Rest is not the absence of work. Going for walks, taking time to read, + enjoying the quiet mornings are part of the work. We need time + space for our brain to make connections - if it’s constantly flooded with inputs those won’t happen.

15. Avoiding a hard truth doesn’t make it go away. It just keeps growing. Whether it’s a bad hire, the assumption you don’t challenge, or a conversation you keep postponing, deferring it only makes it worse.

16. A small circle of honest people who push you to be better > a large circle of people who only tell you what you want to hear. Always seek out the former.

17. Nobody is going to give you permission. The only thing between you + the next chapter is your decision.

18. Writing is structured thinking. Write to understand what you actually believe or are trying to learn, then share it.

19. Find the problem that feels like play to you but is “work” to everyone else. You’ll outcompete anyone who’s doing it for the outcome because you’re doing it for the thing itself. You escape competition through obsession — and obsession can’t be faked.

20. I've sat in rooms where the questions being asked told me everything I needed to know. When the conversation around you no longer matches the level you're operating at, stop trying to fit. Build a different room.

21. Calculated risk is not the same as zero risk. At some point the foundation is built + the move is just a decision. Recognize + be honest in differentiating between preparation and delay.

22. We have 4 burners on our stovetop: work, family, health, + friends, but we can’t run them all at full capacity at the same time. Every season of life has a cost. The goal isn’t trying to perfectly balance all 4, it’s knowing which ones you’re turning up/down intentionally + making sure it’s actually a choice.

23. Being physically present and actually being there are two different things. The ones who matter most to you can tell the difference immediately. So can you.

24. Consistency is the compound interest on everything that matters. Whether it’s in the gym, work skills, relationships, learning a new language, etc., nothing significant gets built in a single effort.

25. Know your ultimate why. If we’re lucky, the work we find is something we love, but that work is there to make the larger life (family, financial/time freedom, etc.) we want possible, not the other way around.

26. The work you do when nobody is watching, for a standard only you set, toward a goal nobody else understands yet - that’s the kind of work worth doing.

This was a fun exercise to go through. Was a good way to zoom out and re-orient around what’s important + the manner in which to go about pursuing those.

Any of these land well with you? Or take it a step further + go through this yourself and let me know what you come up with. I see every reply that comes back to this :)

Book quote of the week

“Success is not a straight line up. It’s fail, learn, try again, then (you hope) succeed. How successful you are is really a function of how well you deal with failure - and how much you learn from it. Many people don’t reach their greatest potential because they fear failure. In avoiding failure, they deprive themselves of a great teacher. Many others fall short because of lack of opportunity, capital, knowledge, or skills. Persistence is an all-important quality on the road to success. (And success presents its own challenges, avoiding complacency being the first and biggest. Which is why, along with kaizen, PBNS - pleased but never satisfied - has been part of our culture since the beginning.)

- Play Nice But Win, by Michael Dell

See you next Saturday,
Sam

It had nothing to do with marketing. Nothing to do with B2B SaaS. Nothing to do with pipeline / demand generation / attribution / revenue marketing / the latest Claude code post on LinkedIn making me feel behind / [insert any other thing that we read/watch/listen to every day as marketers].

Then I hit this line:

“The contribution of any single person to the organization’s purpose is strongly dependent upon the performance of others.”

🤯

I stopped reading.

I read the line again.

“The contribution of any single person to the organization’s purpose is strongly dependent upon the performance of others.”

This line stopped me in my tracks. It’s the GTM ecosystem synopsis I’ve been working through the past few years distilled down to one simple sentence.

…but it was written 40+ years ago about factory floors
…by a physicist (Eliyahu Goldratt)
…in a fiction book called “The Goal”

And this reminded me of a lesson I’ve long known + continue to be reminded of:

Most of the problems we come across aren’t new problems. They’re the same problems as before, just dressed in different clothes.

Subscribe now

Sponsor: HockeyStack

Most ABM programs fail before they even start. I’ve been guilty of this myself + is why I’m approaching it differently this year.

In the past, we’d celebrate impressions served to target accounts like it was a business outcome, but we all know it’s a leading indicator at best. What actually matters is connecting ABM activity to the things that keep the business going - pipeline, revenue, and expansion.

This dashboard from ABM king Andrei Zinkevich + HockeyStack is the closest thing I’ve seen to what that looks like in practice.

The beauty of this dashboard is that it’s truly all-encompassing. It’s not just net new revenue or “impressions served to target accounts.” Just a few of the items you can see with this:

→ Net new revenue from ABM campaigns
→ Expansion revenue from ABM campaigns
→ Renewal revenue from ABM campaigns
→ Funnel metrics from current deals in pipeline
→ ABM penetration by stage
→ High-intent leads without deals
→ Account engagement by company
→ Website “high intent” account journeys

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Ecosystems, not channels

When I wrote about ecosystems vs. channels, I defined GTM ecosystem success as:

“An ecosystem means all of these various touchpoints, from trackable to untrackable, work in harmony with one another to foster and drive the desired outcome. Ecosystems die if you remove certain aspects of them, or if they have too much of something, as there are upward and downward impacts of that element’s presence.”

The questions I was really trying to answer were things I’d experienced over the years + could feel, but never had the “hard data” to prove. Questions like:

• Are BDRs more successful keeping a prospect on the phone if they’ve seen multiple ads first?

• Are marketing emails more likely to be read if a peer mentioned the brand in a community first?

• If an overly aggressive AE called a prospect last year, are they more defensive when a new one calls this year?

These are questions about interdependence. They’re about how the contribution of any single touchpoint can’t be separated from everything around it.

Goldratt was saying the same thing in his book about people, machines, + the fundamental nature of systems:

“The contribution of any single person to the organization’s purpose is strongly dependent upon the performance of others.”

Now just replace “person” with channel, campaign, team, etc. and cue the “aha”…

This is why channel-level optimization is the wrong frame. It’s optimizing a single channel in isolation (AKA solving for local performance) while ignoring system output (AKA global performance).

You can have a BDR team hitting every activity metric + ad campaigns delivering strong CPLs + email open rates that would make any demand gen manager proud…and still have flat pipeline.

And it’s because the result/goal we’re after doesn’t come from each part independently, but the interplay + cohesion (or lack of) them all together.

This is where the concept of force multipliers emerges from ecosystems. They don’t exist inside of individual channels or teams - they’re the coefficient that gets added in front of the GTM ecosystem equation.

Goldratt proved it in his manufacturing example back in 1984. Meanwhile, we’re still arguing about it in B2B marketing in 2026 + still don’t have a solution.

Common sense ≠ common practice

Most of us already know this intuitively because we’ve felt it.

To continue with the BDR example, I started by career as a BDR and can tell you firsthand the difference between how a call went with a prospect who’d never heard of us before compared to one who’d been consuming our content for months or had a peer tell them about us.

So why do we keep optimizing everything in isolation?

Goldratt has an answer for that too. There’s a dialogue in “The Goal” that I keep coming back to:

“We refer to something as common sense only if it is in line with our own intuition. When we recognize something as common sense, it must be that, at least intuitively, we knew it all along. Why is there so often the need for an external trigger to help us realize something that we already knew intuitively?”

“Probably these intuitive conclusions are masked by something else, something that’s not common sense.”

“What could that be?”

“Probably common practice.”

Now read that again.

Common practice is what buries common sense.

We’ve been told for years that the right way to run marketing is to track everything, attribute credit, optimize for CPLs and CTRs, and anything that can’t be measured…well, as long as the company is doing well “you can keep doing that cute podcast of yours,” but as soon as a bad month or quarter hits, that conversation quickly turns into, “Oh yeah, that little unattributable podcast” or “all that time you spend on LinkedIn - yeah that needs to go because it’s not showing up in my reports.”

That scenario has been repeated so many times across companies + people that it became the default due to the volume of it. It became accepted as “the way things are” in B2B because it became a shared experience by so many of us + what company leaders told us to do (because they’re the smart ones, right?…right?”)

Anyway - somewhere in this process, our intuitive understanding of how buyers (and ourselves) actually behave when making purchase decisions (AKA non-linear, messy, multiple people involved) got buried under the accumulated weight of common practice (AKA linear funnels, sequenced campaigns, decisionmaker is also the end user).

Enter: the Socratic method

There’s a second half of the dialogue I quoted above in the common sense vs. common practice section. After they came to the conclusion of common practice being what masks common sense, the character goes on to say:

“Jonah’s way of leading to the answers through asking questions, his ‘Socratic approach,’ is very effective at peeling away the layers — the thick layers — of common practice. I tried to explain the answers to others, who needed them as badly as we did, but got nowhere.
You know, it’s amazing how deeply ingrained those things are that we’ve been told and practiced, but never spent the time to think about on our own. ‘Don’t give the answers, just ask the questions!’”

This hit home for me as someone who’s spent years trying to get marketing, revenue leaders, + broader leadership teams to understand the GTM ecosystem philosophy.

The explanation doesn’t work with them. It hasn’t worked for me, + TBH it probably hasn’t worked for you either. You can show them the data. You can walk them through the logic. You can build the most compelling spreadsheet + presentation of your career about how channels work together + how the attribution model doesn’t account for the interplay. And you’ll get polite nods, a pat on the back for the time spent pulling it all together, + then we get to watch them go back to asking us to optimize CPLs + CTRs the next day.

This is because the common practice is the framework they use. It’s become their ingrained belief about how business growth + the world works. And unfortunately, we can’t argue someone out of a belief they hold dearly, especially one they didn’t reason themselves into in the first place so they feel defensive when asked to justify it.

But what we can do is ask better questions.

Since my time at Refine Labs, I realized I’ve been doing this for years without ever connecting it back to Goldratt/the Socratic method. Here are the questions that have consistently worked for me:

1) “Would you rather hit your lead goal, but miss your revenue goal? Or miss your lead goal, but hit your revenue goal?”

This is my favorite question to ask (sorry, no gradual build in in this list, I’m starting out HOT) + does more work than any slide deck or data ever can. We aren’t arguing that leads are a bad metric. We’re asking them to say out loud, in their own words, what actually matters here. And when they do, we’ve guided them to the conclusion themselves.

2) “Tell me about the last purchase you made for the business. What brought it to your attention? How did you go about the path to purchase?”

Take your time with this one. Let them actually walk through it. You should hear things like:

• A podcast they listened to

• A peer who mentioned the product/service to them

• A LinkedIn post from the CEO

• A Google search/LLM conversation three months later when they heard we were struggling with XYZ

The beauty of this is that by sharing all of this, they’re listing out the non-linear, partially untrackable, ecosystem-driven journey they just told us doesn’t exist. This realization lands best when it comes from their own story.

3) “What’s the most important instrument in an orchestra?”

Ask a conductor this + they’ll look at you like you’ve lost your mind. Ask it to a room of revenue leaders debating whether marketing or sales or BDRs deserve credit for a deal + watch the room go quiet.

Once we get past the tackiness of the question, it helps reframe the GTM ecosystem in something they can easily visualize + already understand.

Everyone knows an orchestra doesn’t have a single most important instrument. The magic of it is the interplay + harmony that comes from the aggregate.

Remove any single instrument + the output degrades. Same thing happens with our GTM motion.

In the book, Jonah didn’t explain the theory of constraints to the factory manager. He asked questions until the factory manager could see + understand it himself. The solution was always there, just buried under years of common practice + the questions he asked simply cleared the path to the factory manager arriving at it himself.

And that's the job of anyone who actually understands how GTM works. We could go in front of leadership/the board and talk about how we’re right about XYZ and that the current way is “wrong,” but I think we both know how that will go for us. Our job is to ask the questions so that they can arrive at the same conclusion + have the same core understanding of how the system operates, regardless of what “common practice” metrics say about it.

Goldratt wasn’t writing about marketing. He was writing about physics applied to operations (and if you really want to get meta, he did the same thing there by bridging physics to manufacturing as we are this book to marketing).

This is why I love reading books + learning from other disciplines outside of marketing. We think we have these unsolvable problems or that new questions are coming up in our space, but the reality is that most of the problems we come across aren’t new problems. They’re problems that have been encountered before, just dressed in different clothes.

A physicist looked at a factory floor in 1984 and saw something most operations managers had stopped being able to see…

Book quote of the week

I think you know what the book quote of the week already is based on this week’s newsletter topic :)

See you next Saturday,
Sam

This was a question my friend Justin Norris asked in a comment to last week’s newsletter about common funnel issues. I thought it was a great question. Some of you may have been thinking it as well, or some of you may encounter a scenario over time where this question becomes relevant.

It’s a hard question to answer definitively as there’s no one “right answer” to it, but in the mindset of these being marketing meditations, I sat down with Justin’s question + here’s what I ultimately came up with.

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Simply reply back to this email if you/your company is interested or drop me a DM on LinkedIn.

But what about brand?

This is essentially what Justin’s question was asking.

How does spending more/less on it change things?
And how does (or doesn’t) this fit in with the models + numbers shared last week?

After sitting with this question for a minute + going past the superficial “most companies have a brand budget and a demand budget” response, I realized it was an answer that was obvious in my head, but when reflecting on it, is not something that’s widely adopted/accepted in our space.

The reason for this is that we can’t optimize our funnels without thinking about how brand comes into play. BUT, the hard part is where brand does affect the funnel is rarely explicitly called out. We all can feel what happens when brand impacts our funnel, but surprisingly it’s not brought up in many conversations.

So with those two cliffhangers (what was obvious to me and where does brand affect the funnel) now lingering, let’s unpack them.

Brand vs. demand → brand + demand

Brand and demand aren’t separate. They’re two expressions of the same thing - building preference within your market.

I personally view them as one and the same (yes, I know they aren’t in reality, just hear me out…). To me, good marketing bridges both at the same time.

That said, as I really think about it, I find that I skew heavily toward brand. But why?

The power that a strong brand association can create, the long-term recall seeded into the market for what you want to be remembered for, the virality/word of mouth that can occur when you have happy customers, etc. - how those play out shows how brand is a MUCH stronger lever AND lasts far longer than many of the traditional “demand gen” marketing levers, especially those geared specifically for problem aware/solution aware audiences.

At the end of the day, no one really wants to buy software. They just want to solve a problem more easily OR use it to be able to make more money. So when we do go to market to purchase something like software or services, emotion plays into it more than we may be willing to admit.

Yes, there are very cut + dry boxes that need to be checked. “Does it have XYZ functionality” etc., but when we actually go on to making the decision of who we buy, some boxes that will never show up in the comparison are things like:

• Do I like the sales rep we’ve been working with?

• How will recommending company A vs company B make me look when presenting this to leadership/the board?

• etc.

And you know what category those elements fall into? Brand. That’s all about company DNA, how they hold their team members to operating, and their perception in the marketplace.

That’s why brand is such an under-invested in item. It’s not always a function of dollars or separating out ads that are focused on your logo vs. ads focused on a product UI shot.

It’s the standards the team is held to that show up in how they engage with prospects + customers. It’s the little details executed upon at a local event with 15 attendees. It’s having an actual POV that the market also feels and as a result draws them to you because it’s a company that finally “gets” them.

Where brand hits in the funnel

Pulling an example funnel from last week’s newsletter, let’s say this is your current funnel. Before you scroll down, where do you think having a strong brand would improve your funnel? Which variable in here?

Trick question. TBH, the answer is “where doesn’t brand hit in the funnel?”

When you have a strong brand, you’ll see it show up in multiple places here:

• Demo - SQO rate (prospects are being organically pulled through the funnel vs. pushing/forcing them through)

• Cost per SQO (while cost per demo may be higher by not forcing prospects through the funnel, since they convert at significantly higher rates, that means you’re driving REAL pipeline at a much lower cost)

• Win rate (they want to choose you, they just need to do their due diligence)

• ACV (in tandem with the above, you don’t need to dangle discounts or special deals in front of them to convince them to buy)

If I had to point to just one of these though as where it hits “hardest,” I’d say it’s in the demo - SQO rate variable. That’s where there’s the most volume available to be impacted (funnels are a numbers game, after all).

In a “standard” funnel where a prospect is pushed/forced through, this number is typically low and, as a result, means the funnel gets narrow very quickly.

In a funnel where there’s a strong brand involved, this number is typically high and, as a result, means the funnel stays much wider as most of those are qualified.

This is why I like brand advertising more than traditional demand gen/performance marketing ads. Those are trying to capitalize on a very specific time for the prospect where they’re problem aware/solution aware AND actively evaluating. The problem here is they’re wired more in shop/compare mode than “ooo, I like this brand” mode.

Brand gets out ahead of this well in advance of problem aware/solution aware. They’re simply out there existing + consistently staying in front of the market ultimately saying, “I see you and understand you.”

This is what develops trust. And that trust is exactly what drives the higher demo - SQO rate when they enter the funnel.

They trust us. They know what we’re about. They see we aren’t just trying to make a quick buck off of them based on the time we’ve spent in front of them. So they’re asking different questions in the demo. They’re looking to confirm their decision, not be persuaded. Better fit prospects in the funnel + easier conversation for the sales rep = higher demo - SQO rate.

Quick: you need to make a recommendation for a sales CRM for your company right now, who are you recommending?

That’s brand at play.

I’ve spent years optimizing funnels and improving all of the demand levers available to us.

Cost per demo? Tighten the targeting to true ICP + watch wonders happen. Demo - SQO rate? Let the prospect schedule the date/time of the demo when filling out the form. The list goes on (what was covered in last week’s newsletter).

But when you zoom out + look at larger datasets, there’s also a more binary variable that I can apply to quickly assess how strong a company’s funnel is:

Their brand.

If no one knows who you are or they don’t trust you, you can have all of the right demand optimizations built into your funnel, but it’ll still be a weak funnel.

Then on the flip side, if you have a strong brand + people trust you, you can have just some of the right demand optimizations built into your funnel and/or mediocre demand gen tactics in play, and it’ll be a stronger funnel than the one above.

In the past, I’ve talked about this under the context of brand awareness relative to demand creation. And it holds true here as well as this is where the force multiplier effect comes into play.

This was the moment of clarity I had when thinking about Justin’s question. It was realizing my definition of brand isn’t the traditional “brand awareness” definition that covers the first two items in the above equation (I know what you do + I know why I should choose you). To me, brand also needs to contain the third, and most important, element - the ability to make your market want to choose you.

This is the force multiplier of having a strong brand.

The brand coefficient

We need to stop separating brand + demand in our org charts, budgets, + strategy.

They aren’t opposing forces competing for the same dollar to be allocated to them. Brand is what makes demand gen actually work.

Demand gen gets people in the door.
Brand makes them actually want to walk through it.

The companies that have figured this out don’t talk that much about “brand budget” vs. “demand budget.” They intuitively understand that it’s about building preference while they’re building awareness - same effort, just viewed through a different lens.

This is why I can help you optimize your cost per demo down by 50%, but it still won’t matter if you don’t have a good brand/nobody wants to buy from you. And on the flip side, why having a strong brand makes mediocre demand gen tactics work better than they should. (This has always been one that drives great demand gen marketers crazy - “Our campaign is so much better than the market incumbent’s. Why aren’t we getting more demos???”)

Ultimately where this all takes us to is that we need to stop asking “should we invest in brand or demand gen?” + start asking “how do we strengthen our brand coefficient?” This is where the real leverage lies as at that point, we aren’t deciding between two things - we’re multiplying the effect of one with the other.

And this plays out in the following way:

Your funnel gets wider.
Your conversion rates improve.
Your sales team has easier conversations.
Your customers stick around longer because they actually chose you, not just defaulted to you.

That’s the brand coefficient.

Book quote of the week

“In Silicon Valley, nerds are skeptical of advertising, marketing, and sales because they seem superficial and irrational. But advertising matters because it works…It’s easy to resist the most obvious sales pitches, so we entertain a false confidence in our own independence of mind. But advertising doesn’t exist to make you buy a product right away; it exists to embed subtle impressions that will drive sales later.”

- Zero to One, by Peter Thiel

See you next Saturday,
Sam

And if you’re at the same place for long enough, you’ll probably come across the other 3 as the company grows.

If you’re reading this newsletter, you’re a savvy GTM practitioner. You know how + where to gather relevant data from to inform your plans. For today’s newsletter, we’re going to get tactical - breaking down your current funnel, diagnosing what’s going on inside of it at critical points (whether good or bad), AND then going over what we can do to set ourselves up for success moving forward.

Let’s get to it 🤓

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→ Website "high intent" account journeys

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First things first - the funnel itself

MQL. PQL. SQO. SQL. Stage 3. Handraiser. Download.

The list can go on literally forever. We’ve come up with more acronyms than we know what to do with. And every company usually has their own unique combination of them which makes comparing performance always subject to the “well, we’re unique!” line (note: our setups really aren’t as unique as we think).

For this exercise, like most things, simplicity wins. So for today’s newsletter, we’re going to keep with that simplicity as it relates to the funnel. The heavy majority of B2B companies operate off of a sales-led motion (SLG), even if they have a product-led (PLG) motion that complements it. For today’s newsletter, we’re going to focus on the sales-led side.

Here’s the basic funnel that we’re going to use:

The cells in green are your inputs:

• Variable spend (think: ads, events, etc.)

• Demo requests (if your company is predominantly PLG, simply update this to be signups)

• Opportunities created (I would recommend this being the stage at which your company considers them qualified)

• Opportunities won (this one’s straightforward)

• Total ARR/annual recurring revenue (how much revenue was booked per 12 month basis)

Now it’s your turn to start playing. Here’s a link to a sheet you can use for this exercise - simply make a copy + you can start dropping your own numbers in.

Once you fill in the green cells in the tab titled “Baseline,” you’ll now have your…wait for it…baseline!

And now that you have that baseline documented, let’s quickly talk about the key growth levers:

Now we have some new cells highlighted in green here. These are your key growth levers that you can control.

• Variable marketing spend

  • Add more spend to what you’re currently doing. More $$ behind ads, more microevents hosted, etc.

• Cost per demo

  • Tighter targeting + focus on better fit prospects (ICP)

• Demo - SQO (sales qualified opportunity) rate

  • Get rid of any obstacles that would prevent a prospect from becoming qualified

• Win rate

  • Look at where the majority of revenue comes in (industries, company sizes, regions, etc.) and focus there

  • Bonus: if you’ve done a win/loss analysis, look at the most common reasons for loss + implement solution(s) toward fixing those

• ACV (annual contract value)

  • Right fit prospects don’t need discounts - they understand the value you provide

  • Similar to win rate, when you know where your revenue comes from, you will see differences between firmographic datapoints that may have you exploring how to get more from those specific companies

Now we’re ready to identify which of the 4 funnel issues you may be experiencing.

Funnel issue #1: lead gen 101

If I had a dollar for every time I saw this one back in my Refine Labs days…

This is what the funnel looks like when using the traditional “lead gen” playbook. Everything is gated. Webinars + ebooks + badge scans are the primary lead sources from marketing. Marketing is always celebrating that they’ve hit their monthly/quarterly “lead” goal, but sales somehow misses their pipeline and revenue goals despite “all of the lead volume” marketing is sending them.

To be blunt, it’s because the leads are 💩. They aren’t actually leads, it’s a false top of funnel measure.

How to spot this:

• “Leads” coming through aren’t true demo requests/handraisers - these prospects aren’t ready to start the purchase process

• The lack of quality/premature nature of these show up when you look at the conversion rate between “Leads” and SQOs

• Often shows itself when you see a “too good to be true” cost per “lead”, but high cost per SQO (function of a low lead → SQO conversion rate)

• Even those that make it to the traditional SQO stage often close at a lower rate than they should because they’re being pushed through the funnel vs. being more naturally pulled through it

So in the example above, we see this in the orange cells as a hyper-inflated number of “demo” requests, a “too good to be true” cost per demo of $30, and an abysmal demo → SQO rate of 0.3%.

What you’ll also see in the images in here are a column that has rough industry benchmarks for what good looks like. These will be helpful for you to spot how close/far off you may be (and what’s realistic).

How to fix this:

• Split the funnel by lead sources (demo requests, webinar leads, etc.) to understand if specific programs/campaigns can be optimized/removed

• End programs/campaigns that are budget drains while continuing/iterating

  off those that can be salvaged (specific keywords in search, social

  campaigns with high engagement - understand why, etc.)

• Ungate “lead” assets + let them be consumed for free

• Stop passing these types of false “leads” over to Sales as “qualified”

  • Note: High-intent handraisers like demo requests won’t be impacted as they don’t come in through these campaigns

• Reallocate spend from these lead gen campaigns to efforts that generate more

  efficient handraisers + SQOs

What this looks like as it’s played out over a few quarters:

• Your “demo” requests line is going to decrease drastically. Don’t freak out, this should decrease because what was being counted here before weren’t actually demo requests.

  • Pro tip: make sure you communicate this to your leadership team ahead of time though or you’re going to wake up to a lot of “WTF HAPPENED!?” emails when they get the first report

• Your cost per demo is going to increase drastically for the same reason as above. This is expected + ok.

• Most importantly, you’ll see your demo → SQO conversion rate shoot through the roof compared to before (+ your sales team will start to love you again)

Funnel issue #2: marketing/sales misalignment

You’ve cleaned up the 💩 leads from coming through and have a more accurate representation of who’s coming inbound that are true-fit prospects. But for some reason, even though you know these leads are better, they aren’t converting like you know they should be.

Enter: marketing/sales misalignment

How to spot this:

• Demos/handraisers are measured correctly + are strong-fit ICP

• Similar to Lead Gen 101, dropoff occurs at the demo → SQO conversion rate

  • Since we know we aren’t running “lead” campaigns + are reporting on true

    high-intent handraisers, lead gen 101 can be ruled out

• Marketing/Sales misalignment is often the cause of the dropoff here

  • Sales reps are historically used to marketing sending poor leads, so they

    don’t follow up on these as they expect them to be similar

  • There’s a constant game of phone/email tag to try and coordinate the discovery call

  • Discovery call frustrations from answering repeat questions they’ve already answered on forms, from talking to BDRs, etc.

• Even with a great sales team (win rate), this isn’t efficient due to few SQOs

  available to be won

So in the example above, we see this in the orange cells as a very low demo → SQO conversion rate and a resulting very low number of SQOs.

How to fix this:

• Determine why + where the dropoff is occurring

  • Sales not following up?

  • Backend processes not sending data correctly?

  • Phone/email tag between SDR/prospect to schedule?

  • Prospects frustrated they can’t get simple information? (Pricing, demo, etc.)

• Implement the correct fix(es) as needed

  • Align with sales leadership on demo request follow up process

  • Dig into marketing automation to determine where data isn’t passing

  • Look at a solution like Chili Piper or Calendly to allow prospects to schedule meeting when it works for them + avoid the back and forth of trying to coordinate that call via email

  • Set expectations clearly on demo form, have pricing publicly available

What this looks like as it’s played out over a few quarters:

• Your demo → SQO conversion rate will pick up quickly

  • The 1-2 punch of telling the sales team “hey, we’re sending you people who actually want to talk to you now” + letting prospects schedule a day/time for the demo as soon as they fill out the form cleans up the 2 biggest reasons for dropoff between these 2 stages

• Your number of SQOs will increase significantly simply as a function of the increased conversion rate

Of the 4 funnels, this one is the most common AND most easily fixable. Just requires open communication between GTM leadership, aligning around the right strategy, and adding 1 tool to the mix (calendar scheduling). Then you sit back + watch the pipeline pour in.

Funnel issue #3: poor product/market fit

This one shows up more often in earlier stage companies or in companies that have rolled out new products, expanded into new markets, changed their plans, etc.

How to spot this:

• Demos/handraisers are measured correctly + are strong-fit ICP

• Strong demo → SQO conversion rate

• Dropoff occurs at win rate - analysis on loss reasons shows majority come from

  loss due to things such as: “Price”, “Functionality”, and/or “Competitor”

• Common causes for this:

  • Company wants to go “upmarket”, but product isn’t able to support this yet.

    Product built to meet SMB/MM functional needs (think: Hubspot), but priced

    as if serving enterprise (think: Marketo) - you’re too expensive for those who

    want it, but not comprehensive enough for those who can afford it

  • Missing critical features/functions that are needed in prospect’s role or that a competitor has

  • Your offer is a commodity in the market + the same service level/features

    can be found at competitors for less

So in the example above, we see this in the orange cells as a very low SQO → win rate, a resulting very low number of won deals, and a very high customer acquisition cost (CAC).

How to fix this:

• Perform win/loss analysis + look at the top reason for loss buckets

• Discuss with product marketers, marketing leadership, + sales leadership as needed

• Implement the correct fix(es)

  • Trying to go upmarket

    • “We’re targeting upmarket + pricing at that level, but the product isn’t able to support their needs yet, while SMB/mid-market are actively requesting to purchase, but are being turned away. We need to find a balance of supporting both and grow into upmarket”

  • Price

    • “When we see this many people reach mid-stage opportunity but a low win rate with pricing as the reason for loss, that tells us they see the value + want the product, but it’s not affordable for a company like them”

  • Functionality

    • “When we see this many people reach mid-stage opportunity but a low win rate with functionality as the reason for loss, that tells us we’re missing a key product feature that’s necessary for the prospect to do their job well”

  • Competitor

    • “When we see this many people reach mid-stage opportunity but a low win rate with competitor as the reason for loss, that tells us their product is either better, offers more features for the same price, or offers the same features/better service for a lower price”

What this looks like as it’s played out over a few quarters:

• Your win rate will significantly increase as you’ve fixed the things that prevented prospects from buying

• The number of closed won deals + corresponding booked revenue will take off up + to the right

• Your CAC will drop off to a much more reasonable + scalable level

Funnel issue #4: unrealistic goals

And that leaves us with the best for last - unrealistic goals 🙃

Huge growth targets. A leadership team + board that are deadset on hitting it…

…and a slight disconnect from reality when you start looking at the numbers.

How to spot this:

• Everything is measured + defined correctly (leads are actual leads, SQOs are actual qualified opportunities, etc.)

• Conversion rates + CAC payback are well above benchmarks

• The only funnel “problem” is that the revenue generated is falling short of the revenue “goal”

So in the example above, we see this in the orange cells as the ARR booked is less than the ARR target given to us. Everything else is very healthy.

How to fix this:

• The only main lever we can pull is at the very top - the amount being spent across paid media + content production costs

• Share where we can spend more before seeing diminishing returns

  • Paid search:

    • Impression share lost due to budget

    • Add additional high-intent keywords

    • Expand into Microsoft Ads

  • Paid social:

    • Reach is < 40%, penetration is < 80%, and/or frequency is < 10

    • Add additional campaigns/mediums (more educational content, videos, etc.)

    • Explore other platforms like Reddit, Twitter, Facebook, etc.

    • Expand organic social presence

• Most importantly: Ask to better understand how the goals were calculated and what assumptions were made that led to the goal being set

What this looks like as it’s played out over a few quarters:

• Your ARR will increase as you put more resources into play

• BUT, this comes with the following “costs”:

  • You will have to spend more on variable marketing (ads, agencies, etc.)

  • Your cost per demo is probably going to increase (growth isn’t linear + there is a point of diminishing returns)

  • Your CAC + payback periods are going to increase

    • This last one is OK! Because you were so efficient before, you were actually leaving money on the table at the expense of growth

    • This doesn’t give you permission to go crazy on spending, but this is when you should be having a conversation with leadership about what’s being left on the table if high growth is the true expectation

Example: where you should start

You probably don’t fit perfectly into one of these “common” funnels. You might have some aspects of one funnel + some aspects of another. What you do know is that there’s room for improvement, but you just aren’t sure where to start.

Based on everything we’ve covered above, here’s an example funnel that’s probably closer to something you are or have experienced + how I would recommend going about optimizing it.

What jumps out to you in here?

Take a moment and think about this. I’m going to give you some scroll time so I don’t spoil the answer for you with what’s below

…

…

…

…

…

Here’s the order I would tackle it in

1. Demo → SQO rate (marketing/sales alignment)

   1. We can insert common fixes quickly here (prospect schedule meeting, fix internal data syncing, kickoff better marketing/sales alignment)

2. Demo quality/volume (lead gen 101 or broad targeting)

   1. This is often seen after 1-2 quarters of our programs running. We will absolutely influence this number, it just takes time to play out

3. Win rate (product/market fit mismatch)

   1. A result of the above + the length of their sales cycle

4. Annual contract value

   1. This one + #5 shouldn’t be done UNTIL the first 3 above have been addressed

   2. This will be a function of better targeting, truly understanding your ICP and who values your product/service, AND then some fine-tuning of your plans/offers

5. Variable marketing spend

   1. Don’t touch this until everything above is efficient + firing on all cylinders, otherwise you’re just burning cash

Which leads us to how this looks as it’s played out over the following year:

A thing of beauty.

Don’t get caught up in the dip in demo requests, you’re generating more SQOs now than you did before with that first emphasis on increasing demo → SQO rate.

Everything else cascades as a result of what we covered above if you take things through those 5 steps. Then you get to sit back, give yourself a pat on the back, and can finally take a breath in knowing you aren’t playing constant catch up to your goals.

Now what?

You’ve got the framework + you’ve got the spreadsheet to toss your data into. Now the question comes down to understanding what’s going on in your funnel.

Grab the spreadsheet + fill in the input (green) cells. You’ll quickly get a sense for what is/isn’t working + will either validate something you may have been feeling already or may be the unlock you needed to get to the next stage of growth.

I’ve gone through this exercise with well over 100 companies + I love it because it flat out works. It’s simple + points out what’s going on.

Some can run with it solo from here to see where they stand + act on it from there. Others need help translating the diagnosis and/or acting on it. Either way, you now know how to approach this exercise + that’s half the battle.

If you need help or want to walk through yours together, simply hit reply. Replies to this come directly to my personal email + I’m happy to help figure out next steps.

And because this was a long email, here’s a link to that sheet again just in case 🙂

Book quote of the week

Since I brought up John Boyd earlier, it was only fitting to have something from his biography this week:

“We were each given a mystery solution containing half a dozen or so compounds. Each solution was different. Our task was to identify the compounds. The grade depended on how many you could identify. Mine was a clear solution with absolutely no clue to its ingredients. We had four weeks to decode it.

There were two different ways of going about the analytical process. One was by following preordained steps, rigorously identifying some compounds and eliminating others step by step by step. If you did everything correctly and interpreted your results correctly, this was bound to lead to the correct result - eventually. However, this rigorous process was extremely cumbersome and time-consuming, and there was a danger of running out of time.

Alternatively, you could make your own path. You could start with the rigorously mandated, conventional process, but as the results unfolded, you could take an intuitive leap and make up your own sequence of experiments, adjusting them as more results became available. This method had the advantage of being much more direct and faster, but it was more risky because if your experimental flow went in the wrong direction, you could blow the whole assignment.

I was confident enough in my grasp of inorganic chemistry to choose the high-risk option. After a few steps, I departed from the predetermined flow and, keeping careful notes, struck out in a direction that seemed logical to me.”

- Swimming Across, by Andrew Grove

See you next Saturday,
Sam

THAT'S 👏 BECAUSE 👏 LEADERSHIP 👏 HAS 👏 THEIR 👏 TEAM 👏 DO 👏 THE 👏 RESEARCH

Unless you're targeting small companies, an effective leader often delegates buying research to the members of their team who would benefit from the purchase.

If you ever want to see me get HEATED about a subject, this is one of them. Let’s talk about why…

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Sponsor: You/Your Company?

If you’re looking to get in front of an engaged audience of some of the savviest marketers + GTM practitioners, this is your opportunity. One opening per month to sponsor this newsletter has become available + I’m sure will claimed quick, so if the audience reading this newsletter is your ICP, this is your chance.

A few weeks ago I was talking to a VP of Marketing + they said they were exploring/in negotiations with one of the sponsors of this newsletter after learning about them here + seeing them as a product that I endorse. That’s the power of these types of partnerships done well (vs. the AI influencer dumpster fire some are experimenting with).

Simply reply back to this email if you/your company is interested or drop me a DM on LinkedIn.

📚 Story time 📚

A client I worked with years ago while at Refine Labs with had an inbound demo request come in from a perfect fit ICP prospect. Like tier 1, check allllll the boxes, “would love to have their logo on our website” perfect fit.

...but the job title associated with the submission was "Intern."

Since we tracked all of their inbounds, when I saw that demo request come through, I was STOKED + sent them a message of congratulations and to hear how they were going to make sure they got the red carpet treatment.

Turns out, they were about to disqualify it. It wasn’t the right “persona” since it was an intern.

A few deep breaths and goosfrabas later, I challenged them to give that intern a call. I told them about how I had been in positions like that before where I was doing research for our company’s decision-makers.

Fast forward a couple of hours later + I got a note message back from them:

"So, we had the discovery call with the intern and he's working directly for the CEO. Was tasked with researching which solution they should purchase to solve what they're going through."

The next call with the account was the demo, and guess who was on it - the CEO.

What the data tells us

Peep Laja hit on this earlier this week with this post on LinkedIn:

Two BIG stats to recognize here:

• 82% of CMOs enter after the team has already narrowed down the list

• 35% only at the very final stage

AKA, if you’re optimizing for the executive only with your targeting, you’re fighting with your hands tied behind your back.

The execs aren’t doing the research or taking the discovery calls - they’re having their team do that. Or to pull from the post above, "My team does the first two rounds. I come in for the final 2-3 vendors when it's time to make a call."

What we need to learn/remember here

Unless you're targeting small companies (1-10 employees), an effective leader often delegates software/services research to the members of their team who would benefit from the purchase. They’re the individuals who are feeling the pains, not hitting targets, or are tasked with solving for how they’ll hit increased targets. And since they’re the closest to the problem, the savvy executive lets them do the initial research + vetting.

While the individual who signs your contracts may be the CEO/CFO/CMO/VP/etc., more often than not, they're only involved later in the process after their team has done their due diligence.

So all of those ads targeting execs, BDR calls to leadership teams, etc., are far from the best use of your resources.

The people deciding if you make the initial shortlist are 2-3 levels down from them. They’re the directors, managers, individual contributors, etc. who would benefit from the purchase.

By the time the exec shows up, you’re either on the shortlist or you aren’t. The team has decided if you’ll be involved when the decisionmaker gets pulled in.

So what this means for us as marketers + GTM practitioners is this:

🙅‍♂️ Do NOT automatically DQ an inbound handraiser who fits your ICP but their title is "too junior"

🧐 Know ALL of the job titles of your product’s end-users within your ICP + target them

The ultimate decisionmaker is often too far removed from the pain - the employees who would benefit from your solution are the ones who will advocate up the chain for you.

That said, you still need to have some inkling of mental mindshare with the decisionmaker so that when the final 3 options bubble up to them, they recognize your name over the others, that you've somehow demonstrated credibility earlier on with them.

That's what takes you from 1 of the final 3 to "tell me why we shouldn’t go with [brand]."

Book quote of the week

“And it became the place where [Jobs] really learned, albeit slowly and reluctantly and against his natural instincts, that sometimes the best management technique is to forgo micromanagement and give good, talented people the room they need to succeed.

- Becoming Steve Jobs, by Brent Schlender

See you next Saturday,
Sam

Not because we didn’t have enough information, we had plenty. The problem was in some instances I was starting to blur the line between “I need more info to make this decision” and “I’m seeking additional info to confirm my decision” (aka confirmation bias).

This showed up in 3 places: evaluating different vendor sets for 2 different use cases we needed software for on our marketing team + deciding on the AEO approach we’re going to be executing this year.

Unfortunately, this is a trap I see regularly - we get stuck in research mode, gathering data, talking to more vendors, reading more reviews, talking to peers, + waiting for 100% confidence before we move.

So I reflected back on this week + what I had us do to break out of this cycle.

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Sponsor: HockeyStack

For the past 2 years I've been asking myself the same question over + over again:
"What does an ideal GTM ecosystem journey actually look like for our ICP?"

...but I still don't have a *clear* answer

I know the answer exists + that it's hiding in our data. I know that if I could actually see it, I could craft our GTM execution around it instead of guessing. But every time I try to piece it together, I get stuck at the same point:

"Are BDRs more successful if they've seen ads first?"
"Do the order of activities impact one another?"

So we're all sitting here with tons of unstructured data that could answer these questions, but don't have the infrastructure to actually surface the answers we're after…until now.

HockeyStack launched Blueprints recently + it's the first tool I've seen that finally shows which activities + sequences actually happen when we WIN and what is (or isn't) happening when we LOSE.

Check it out

From strategy > execution

We’ve been mapping out our approach to SEO/AEO content for weeks. And I’ve been feeling the paralysis creeping in - there were always more questions, more nuances to explore, more data needed to understand what direction to go, etc.

The trap here is that strategy work feels productive. We’re thinking, we’re planning, we’re gathering more context, we’re making data-informed decisions, and so on + so forth. But eventually, we’ve got enough to be confident in the direction we need to move in, so the “we just need one more week of planning” becomes procrastination disguised as diligence if we’re being 100% honest with ourselves

So I set a hard deadline: “By [date], we’re moving from strategy + planning to execution.”

That deadline wasn’t arbitrary or an ASAP date - there was plenty of time between when I set it + when it arrived (aka enough time to prioritize any remaining details we needed). But it forced us to answer the real question: “do we have what we need to start?” And the answer to that was yes.

Now we knew what to do in the time between when we set that date + the “start executing” date. We stopped researching + started planning the execution.

What are the macro tasks?
What subtasks roll into those?
What sequence does this need to occur in?

We knew what we needed to do. Now it was just a matter of mapping it all out so that it would happen.

We all know that we need to know our DIRECTION first. What we’re trying to accomplish, what success looks like, etc. But one thing I’ve learned over the years is that knowing your direction means NOTHING without VELOCITY behind it. Velocity is the action. It’s taking the first step + making progress toward the plan we created.

For years I got this backwards. I’d think, “I need to know everything before I move.” But what I’ve realized is that it’s, “I need to know the direction, then I need to move, then I can adjust based on what I learn.”

It’s understanding that we’re not locking in the “final” strategy + it being dogma after that. We’re simply locking in v1 so we can finally take off. Then once we’re in motion + have velocity, we’ll have real data to adjust our direction with. Data we can’t get from spreadsheets or another round of research.

Evaluating vendors

Unfortunately, vendor decisions are a little different from the above. We can’t just “take off” with a tool and adjust - we need to actually choose one.

This is where analysis paralysis gets tricky. We talk to one vendor, have questions, so we then talk to another to compare. Now we’re seeing the differences between them, so we dig deeper. Before we know it, we’ve spent 3 weeks evaluating, have a list of 10+ vendors, then somehow come across yet another one that we need to look at before we move forward in conversations with any of the others.

So here’s what we did this week to stop this cycle: created a scorecard.

One of the tools we need is something to help with gathering AEO/LLM data. So I tasked our organic growth manager to list out the things that actually mattered in making this decision. And he then came back with things like:

• Prompt coverage

• Prompt volume + precision

• Quality of answers + how recent the information is

• Topic clustering capability

• LLM coverage

• Sales rep helpfulness/trustworthiness

• Quality of team (CS to engineers)

• Post-sale support/customer success

• Pricing

• Third-party reviews

• Peer recommendations

We didn’t overthink the criteria - these came directly from what we actually needed to do the job well + to then validate which we were leaning toward. Then it simply became an exercise in scoring each vendor. Some items were on a 1-5 scale, some were binary yes/no responses, some were open-text responses.

Then the magic happened. Once he filled out that scorecard, the decision became obvious to us. One vendor clearly won. It wasn’t perfect in every category, but relative to the others, it had the right combination of what was most important to us.

Pre-scorecard, we could’ve kept researching forever. Post-scorecard, we had the answer.

Two-way doors > one-way doors

My CEO taught me this one + it changed how I think about committing to decisions:

When we’re about to commit to something (a tool, vendor, strategy, etc.), you need to make sure it’s a door you can walk back out of if it isn’t working.

For vendors, that might mean starting with a M2M contract instead of 12/24 month commitments. Or building in an explicit opt-out clause after 90 days if some pre-defined result or milestone hasn’t been met.

For strategies, it means viewing things as iterations. Or as John Boyd, the subject of one of my all-time favorite biographies, defined - we apply the OODA loop methodology. Observe, orient, decide, and act. We execute, we see what happens, we adjust.

But here’s the part that matters - this has to be communicated explicitly when making the decision. “Here’s what we’re doing + why. Then here’s how/when we’ll adjust or exit if it’s not working.”

That explicit statement changes how people perceive your decision-making. We’re not recklessly committing or being stubborn in sticking to “the plan” as it’s written. We’re making the most informed decision possible as time goes on + new data/insights surface.

Once your leader sees how you go about this process a few times, trust builds with them. Eventually we don’t need to say it out loud anymore as it becomes implicit, but we have to earn that by being explicit first.

The cost of waiting

Analysis paralysis feels safe as we feel like we’re being thoughtful + methodical. That we’re gathering info + being thorough. But the’re a cost to this - time spent not making progress toward the outcome we seek. And in a year where I have one goal - exceeding our revenue target - I don’t have time to be paralyzed.

The scorecard + the time constraint solved that for us this week. They aren’t perfect decision-making frameworks, but they forced me to recognize when we had enough information + to move forward with it.

They forced me to shift my thinking. To stop asking “do we have enough info?” and start asking “do we have enough info to move confidently?” Two very different questions, but one can keep us paralyzed forever while the second gets us moving.

Book quote of the week

Since I brought up John Boyd earlier, it was only fitting to have something from his biography this week:

“Whoever can handle the quickest rate of change is the one who survives.”
- Boyd: The FIghter Pilot Who Changed the Art of War, by Robert Coram

See you next Saturday,
Sam

Now that I’m clear on what I need to be spending my time on + truly dedicating time to those items, it’s been time to execute. As part of that, I got super tactical this past week, so I thought this week I’d change up the pace from the last few newsletters that were more strategic/philosophical + share what I’ve been getting into.

TL;DR for today: 3 things you can do that’ll improve your demand gen + marketing efforts ASAP.

In no specific order, let’s get to it…

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Sponsor: MarketerHire

Steve Jobs said the difference between average and great in most things is 2:1. But in software + our industry, it’s 50:1. Maybe 100:1.

Marketing and GTM are moving faster than ever. We have more channels + more mediums than we know what to do with. Product teams are shipping at insane velocities because they’ve adopted AI into their workflows.

...but then we have our marketing teams mostly stuck using the same operating system we’ve used for the past 5 years.

So that’s led to the topic du jour: if product is leveraging AI to ship faster, why aren’t we?

I’ve started seeing MarketerHire’s + their new “MH-1 model” recently. TL;DR of it is they have “elite marketers working in 2-week sprints with AI-augmented workflows.”

The sprint model is what makes this interesting to me. I’ve been talking a lot about focus lately + how most marketing teams have been getting spread too thin, so a model built around a very specific focus on something for 2 weeks + then seeing impact in 14 days is no small promise to make.

For most of us, our biggest bottleneck right now isn’t strategy, but execution. Seems like this is an interesting bridge as it’s less “outsource to an agency” and more “let’s build + run the new system together.”

Start your sprints

1) Win/Loss analysis

This is hands down one of my favorite analyses to run 🤓. I absolutely geek out with our data to find out things like:

• What worked

• What didn’t work

• Which bets are paying off

• Which bets need to end

• Where we should be doubling down

• Where we should be pulling back

• And so much more

To get started, hop into your CRM and create a report using the following criteria:

• All opportunities closed (won OR lost) last quarter/last year/etc.

• All opportunity sources (within same GTM motion - i.e. new customer acquisition, land/expand, etc.)

Next, add the following fields to the columns so you can break them all out in pivot tables + charts:

• Loss Reason

• Win Reason

• Opportunity source

• Company datapoints (size, location, etc.)

• Prospect (contact) datapoints (job title, seniority, etc.)

• Sales team info (team, rep, etc.)

• Date/time info (create date, close date, etc.)

• Incumbent solution info (name, none, etc.)

  
  From there, just start slicing + dicing to uncover a whole world of data to leverage.

2) LinkedIn ads bidding strategy

This is one I get HEATED about. Too often, I see marketers unknowingly outsource their thinking to LinkedIn’s “bidding algorithm” + blindly following that guidance without validating if it’s actually driving the results that are best for THEM - not LinkedIn’s bottom line.

Here are 2 examples so I can show you what I mean + how this shows up:

1. Bidding strategy

Does this section look familiar to you? Most marketers scroll right past it as “Maximum delivery” is pre-selected + we assume this is the best route to take. I mean, how could someone possibly argue with something that says “Get the most results possible with your full budget.”

Butttttt - what happens when you hit the toggle on it to see all of the options? That’s where the magic happens.

In the instance above with an example audience I’ve built out, LinkedIn is “recommending” that I spend $115.12 for every 1000 impressions served. A CPM of $115.12 - are you mad!?

This is telling you exactly what LinkedIn is going to charge you if you let them “optimize” this for you. Certainly no less than $115.12, but likely much more because “similar advertisers to you are also bidding here and we want to make sure you appear ahead of them.” Always so thoughtful to keep us in mind like that, that LinkedIn team.

And those “similar advertisers” they mentioned - LinkedIn is super thoughtful again + provides tons of transparency with the incredibly broad range they’re bidding, anywhere from $73 to $291 in the example above - a factor of 3.5x. Some solid logic here…

This is the least sexy thing you can do with your ad execution, but one I will die on the hill preaching. PLEASE take back control here + use manual bidding. Give yourself a week to calibrate how low you can bid + still hit your daily budget, then monitor from there.

Do this + you’ve just found a way to take back 50-450% of your ad budget. Share this one with your finance team after you do it as well for some extra brownie points (or to justify how you can now fund that experiment you’ve been wanting some budget for 😉).

Poll your customer champions

This is one of the best “hacks” to get past the overthinking spiral we marketers love to find ourselves in.

Whether it’s trying to come up with:

• The perfect homepage H1

• The text on an ad

• The hook for a LinkedIn post

• Who you should have on the podcast next

• A topic area to make a playbook for

• Or any other number of things

Ask your biggest champions. Simple as that.

You most likely already have these users gathered somewhere, whether that’s in a Slack channel, WhatsApp group, community platform, etc. Instead of spiraling for another hour over which specific word to use in a phrase or weighing the pros/cons of prioritizing [topic A] vs. [topic B] for the next month’s worth of content, just ask your champions.

I did this this past week. Nothing overcomplicated. Just popped into our WhatsApp group with the question we wanted an answer to. Created a poll for it with the 2 options we were stuck on, set it live in there, and a few hours later, had the data we needed.

As you can see, that data was WILDLY favored in one direction. And in a moment of quiet humbling, it was not the option I thought was going to win.

Yet another reason why doing these types of mini-polls or pre-validations before shipping something can be so valuable.

Bonus: a masterclass paid media session

Not an ad here, I’m just genuinely looking forward to this one.

YOYABA partnered up with Adam Holmgren (Founder/CEO at Fibbler) + are putting on a paid media masterclass on Feb 12th. I attend maybe 1 webinar/session per month, so when I saw this one + the topic/speakers, I knew this was one where I’ll come away with a few nuggets.

For anyone interested, here’s the link: https://www.yoyaba.com/masterclass

Your turn

As promised, that’s 3 things you can start in on next week + are guaranteed to improve the trajectory of your marketing efforts moving forward.

Give them a shot, let me know what you find, + reply back if it turns up anything interesting :)

Book quote of the week

“His years in the jungle gave him experience rare in the trade. Unlike most of his competitors, he understood every part of the business, from the executive suite where the stock was manipulated to the ripening room where the green fruit turned yellow. He was contemptuous of banana men who spent their lives in the North, far from the plantations. Those schmucks, what do they know? They’re there, we’re here!”

- The Fish That Ate the Whale, by Rich Cohen

See you next Saturday,
Sam

So this week, I started implementing it. It’s not perfect - definitely not perfect actually. I don’t have complete confidence in whether every decision I’m making is the “right” one, but it’s the first step in the right direction. It’s all about building momentum right now + as time goes on, I can make necessary tweaks.

Here’s what implementing this plan has looked like so far:

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Sponsor: Redpoint Insights

Every crowded category has one brand that owns the narrative. They’re the ones publishing proof, not just opinions.

When research is done right, it doesn’t just support your story - it becomes the story your market believes.

That’s what happened with one of Redpoint’s clients, Telarus. They wanted to help their selling partners stand out, not with louder messaging, but with content that actually earned attention.

Here’s what their CMO, Jennifer Dimas, told them:

“We’ve gotten feedback saying that we’re head and shoulders above our competition because we provided our selling partners with something really useful that they can use with their customers to display their expertise.”

That’s what authority-building content looks like. It’s useful, citable, + credible enough that people want to share it.

If you want to see what separates content that gets read from content that gets remembered, check out their latest report:

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The brain dump

As I was prepping for 2026, during the last week of December before we all took off for the holiday break was to write down everything I was currently doing and everything I wanted to do. Wasn’t in a prioritized way, just a “taking inventory” exercise.

The list ended up being a bit longer than I expected. And what struck me wasn’t the volume of it, but that probably 50% of what was on there were “shiny objects.” Something new, doing “more” in terms of channels, testing out something else. Things that are exciting as a marketer, but when zooming out and asking myself, didn’t necessarily translate directly to my #1 goal: exceeding our revenue target.

Those were more of what I ended up categorizing as a “bets” bucket: new initiatives, experiments, things that could be valuable but aren’t yet proven to directly impact revenue generation.

And in a year where I have ONE goal and ZERO wiggle room, those bets need to be just that - big bets that I take on if + when I have bandwidth, not things I’m actively working on and pulling me away from the items I know do impact my goal positively that can’t afford to be neglected.

So I categorized this brain dump list into three categories:

Core work
Things I do every day/week that directly drives pipeline or support the systems that drive pipeline.

Think: ad optimizations, ABM plays, PLG flow optimizations, sales enablement content, podcast recordings that fuel our content engine, etc.

Supporting work
Things that matter but aren’t directly tied to future pipeline/revenue generation.

Think: market research, vendor/customer relationship maintenance, etc. These shouldn’t be cut, but they need to be relegated to “as time permits,” + not at the expense of any core work.

Big bets
This contains everything else. I purposely include “Big” in “Big bets” because with any remaining time/resources we have, if we’re committing to something additional, it needs to have a potential disproportionate upside. If it’s nominal, I keep it on the list, but make a note of that + that it shouldn’t be taken on until we hit on the ones with higher potential.

Think: new initiatives, new channels, new mediums, different ways of executing, etc. These are the “sexy” things that we want to do but aren’t yet proven to be connected to the goal.

And that’s why these live in their own category. If I finish my core work + am tracking to goal, great - let’s get curious + go explore. But they’re not put on my calendar ahead of time. In a way, I use them as a “carrot” for myself to get through all of the core work that needs to be done + then I can explore these.

Bringing it to the team

This quality + focus problem is not uniquely mine. I’d been hearing things from our team that all effectively told me, “I need to know what to focus on and how to tell if I’m making progress toward it.” So I’m taking them through this journey as I go through it myself.

This past week we had a team meeting where I laid out the two primary goals for the company and for marketing. Then I had Elie, a member of our team who’s applied this framework to his own work a number of times, to walk them all through how he’s thinking about this + applying it to his own work.

This was an intentional decision for a few reasons.

First, this bridges it from theory to practice. Everyone on the team knows what Elie does + by seeing how he approaches the goals and ties them back to his day-to-day, they’re able to connect the dots for themselves to see how they should apply it to their roles.

Second, I didn’t want this to be an exercise of me telling them what to do. This was a peer showing them what’s worked for them before + their approach to it. It wasn’t a top-down mandate from me.

And then as we were heading into the weekend, I sent a note to the team that said:

“Something to think about over the weekend
Hey team - now that we’ve spent some time going over how we want to operate this year (focus + 10/10 quality) and have our overarching company + marketing goals, I want each of you to spend some time thinking about how you uniquely can help us achieve those.
What are the 1-3 things that, if you truly focus on + do at a 10/10 level, you are confident will help drive more revenue for us?
Some of these will be daily or weekly tasks + that’s completely ok. There are fundamental things that need to be done regularly because they work. Kobe Bryant would take 800 jump shots every day + that’s why he was the 🐐.
Some of these will be larger “projects” which will require steady progress made over time. The important thing here will be mapping out what steps need to be taken and making sure we’re staying on track with those.
Once we lock those in, we can ruthlessly protect our time + capacity so we can do those things well. Everything else that comes up will need to be evaluated from the lens of, “Does this tie in with the work I’m focused on currently? Will it drive more pipeline/revenue for us? Or is this something that falls into the ‘supporting’ or ‘big bets’ categories?””

The goal of this isn’t to be a micromanager or reduce the scope of roles. It’s to provide clarity. And more importantly, to give ourselves permission to say no to the things that pull us away from what actually matters + achieving our ultimate goals.

What this looks like for me

As I wrap up every workday, the last thing I do is set my “Big 3” for the next day. These are 2-3 items that, if I do NOTHING else over the course of the day, need to get done/have progress made toward.

I started doing this last year because at the end of nearly every day, my to-do list was somehow longer than when the day began. I would reflect back on the day and feel like I hadn’t accomplished enough. So I used this list to basically say “if I do these 2-3 items, no matter how few/many other things I do, my day can be viewed as a success.”

This sounds simple, but it’s surprisingly difficult because it requires thought to weigh out what I could do on the Eisenhower Matrix (urgency/impact). It forces me to prioritize before my day gets hijacked by Slack messages, “urgent” asks, etc.

Then at the end of each day, I come back to that list to note what progress has been made toward them.

Finished it? Love it, cross it off the list.
Made good progress? Great, keep the momentum going + have it on the list for tomorrow.
Didn’t get to it? Why not? Was something truly more important/impactful, or did I get caught up in the day-to-day + get distracted?

Nothing crazy here, just something I can keep front and center for myself every day. As the old saying goes, “keep the main thing the main thing.”

Accountability + visibility for leadership

I restarted the weekly Slack update I send to my CEO this week. This is something I used to do when I first joined Loxo + it worked really well. Helped Matt understand where I was focusing my time + why. Also, there’s just something about being externally accountable to someone (whether they specifically ask for it or by proactively having them be the external party) + putting a “scoreboard” on yourself that changes how I think about my week (and what I act on).

The format is super simple:

What was accomplished this past week
When possible, think outcomes vs. tasks.

Example: “led webinar on [topic]” is a task, but “47 ICP-fit prospects attended webinar on [topic]” is an outcome. I’m training myself to think in outcomes because that’s what actually matters.

What we’re working on next week
Similar to the above, frame this around what results we’re trying to drive. This also helps them to understand what your priorities are + see how what you’re doing ties to larger company initiatives.

Example: “updating the homepage” is vague + doesn’t contain the why behind it being a priority. “Updating the homepage with language more specific to our core ICP” is stronger. This then gives you the opportunity to put what your success indicators are for it, i.e. “This should increase website visit to handraiser conversion rate by XX%.”

What we missed this week
Here I’m being transparent about what didn’t go to plan. The curveballs that came our way + the things that aren’t panning out how we’d like them to. What happened, what was done about it, what's the next step to course correct. Normally we’d shy away from something like this as we don’t want our manager to see us in a “not performing” light, but this actually does the opposite. It builds trust, it helps them see you taking accountability, and it shows them you’re internalizing misses + learning from them vs. hiding from them.

Example: "Didn't hit webinar attendance target of 75 - landed at 47. Root cause here was we only promoted this externally for 2 weeks (vs. our normal 4 weeks) due to [reason]. To course correct, we're [insert relevant resolution here]. Our next webinar is on [date] and we’ve incorporated [reason] into our plan for that so we don’t have that same miss again.”

The version I’m doing now is different from the one I used to do. It’s more concise + outcomes-focused as when I did this previously it was just me on the marketing team so I was doing a lot of execution. TBH I’m not sure yet if this is the final form I’ll keep using - have a feeling it’ll iterate some as my CEO + I have some back and forth on these so that it incorporates everything he wants to see vs. what I think he wants to see.

There’s something about putting your results (good or bad) in writing every week that forces me to be honest, not just about what’s working + what isn’t, but to also force myself to learn + adapt from it.

Is this the right move?

I don’t know yet if this will work. It’s a gamble. It’s a good bit more structure than our team has ever had before.

I know in theory it’ll work because it forces clarity on what matters, incorporates more accountability, + gets indicators in place so we can see if we’re making progress. But as with everything, it’ll come down to seeing how it plays out in practice.

Ultimately this is v1 for us. I’m very intentional about calling things “v1” with our team as there’s an underlying connotation in there that a) it’s the very first version of something and b) that any time you see something like “v1”, you know that there will usually be a “v2”, then a “v3”, and so on. So they understand that we’ll iterate, that this isn’t the final version of how we’ll absolutely be doing it moving forward.

If this is something you’re interested in, let me know + I’ll come back in a month or two with a follow up on this. What’s working, what I changed, where I was wrong, etc. If this is something you’ve already implemented or have gone through yourself, let me know! I’m sure there are a handful of lessons that you learned + skinned knees that we can avoid by learning from those.

Book quote of the week

“When I put all the pieces together, it looked complicated, but each piece was simple. Most big things are simple in the specific, much less so in the general.”
- The Score Takes Care of Itself, by Bill Walsh

See you next Saturday,
Sam

That was what my inner voice kept saying to me when reflecting back on the key initiatives I put in place last year.

This is the dark side of having incredibly high expectations and standards. It drives success (because that’s the only result we’ll settle for), but it also means rarely being at peace with how it played out. We take on things we know we can do well…and avoid/delegate the things we don’t do well.

We don’t celebrate the parts that went well (the expectation is success, so why wouldn’t XYZ have gone well?) and obsess over what didn’t go well, what could’ve should’ve been done better. And as I look back at last year while preparing for the year ahead, I wanted to understand why I kept having this feeling and how I can finally get a better wrangle on it.

Which has led to my 2026 “work resolution.” Just 1, and a very simple 1 on paper, but I know will be the hardest resolution I’ve ever set for myself:

Run toward the pain and attack it with a dogged focus + 10/10 standard of quality.

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Sponsor: HockeyStack

Your CEO just slacked you: “We have our board meeting in 2 days. Send me a slide with what’s working + anything they need to know.”

Did your palms get sweaty reading that?
Or is this an easy ask because you can easily get to this info already?

I’m neurotic about forecasting + tracking performance. I have reports upon reports and dashboards upon dashboards.

So when Emir over at HockeyStack asked me what my perfect dashboard would look like, I immediately started geeking out.

And when they sent this dashboard mock-up back to me, I was in nerd heaven 🙌

2026 is officially underway. And it’s never too late to add some solid reports or views to your dashboard, so hopefully this provides some inspiration to any of you who are looking to level up your dashboarding game.

Check out the dashboard

Running toward the pain

Like most anyone, there are areas of my job that I excel in and naturally gravitate toward and areas of my job that I…well I’m not so good at. And those are the areas that are often the first to be delegated or “deferred” to a later date.

Over the past few years, I've leaned too hard on delegating the "painful" things and big "problems" that I knew would be challenging to work through. We're at the point now with our team + company's maturity where I can't avoid this anymore - I have to confront it head on. Our marketing team has grown 3x in the past year. Our company initiatives + growth goals are only getting bigger. I need to own the path to our company's success, not merely contribute and hope that my effort will be "enough."

As it relates to our GTM team, we have one goal this year. It’s our revenue target. And my CEO was very clear about his expectation of me + our VP of Sales: “GTM must exceed targets.”

He doesn’t care how we do it.
He doesn’t care what challenges we face.
He said you two are the leaders, figure out your plans and make it happen.

On paper, this sounds harsh, but it’s actually a kindness. There is zero confusion about what he expects from us. Nor is he asking us to do accomplish 10 different things at the same time. One goal. That’s it. We either hit it or we don’t.

And because writing here is as much an exercise for me to get my thoughts on paper as it is to hopefully help others who come across similar problems, this has led to me being very honest with myself about what I need to do to orient us toward success - both using my strengths and also recognizing that I need to run toward the pain + items I've avoided until now. And this is where the dogged focus + 10/10 standard of quality elements come in. Over the coming weeks and months, I’ll see how this actually plays out in the work we're shipping.

Dogged focus

“Can we do this?” Yes, we can do anything. But “should we do this?” - that’s the question that actually matters.

When there were only a few of us on our marketing team, we recognized that we could only do so much and put a disproportionate effort behind the things that we did as a result. TBH, this focus is THE biggest advantage startups have over their larger competitors, but many don’t realize it (AKA me) until they’ve started scaling and no longer have that as their default operating system.

As we’ve scaled the marketing team + added a large number of teammates in our other departments, that focus gradually gets pulled in hundreds of different directions. It’s slow at first, not even something we detect. Sales needs assets updated more frequently. Training needs some help with a few videos to include in onboarding new customers (as the growing Sales team means more new customers). Something changes in a core marketing channel, which means we need to add another variable in the ad campaigns we run.

Before we know it, each team member goes from focusing on a few core items to trying to balance 20+ different tasks + requests. I don’t want to say this is inevitable at every growing organization, but I’ve yet to see it not happen in my experience. It’s simply part of what happens when companies grow. We just need to be able to recognize when this is happening, as this is where the path to continued excellence and the path to mediocrity branch off.

And this is why focus is one of the two core themes for myself + our team this year. The more we try to do, the less we actually accomplish. It’s counterintuitive in written form, but in execution, it’s incredibly intuitive. We have all felt the difference between when we’re working on 1 thing with laser focus and when we’re working on 5 things + getting overwhelmed.

In marketing + the broader B2B world, there will ALWAYS be plenty of good ideas for things we can do. But where focus comes in is asking ourselves should we do this? More often than not, the answer is no because saying “yes” to it would mean pulling focus from what’s actually important AND forcing a decision to be made if we were to take it on: we either go past our capacity to execute and need more hours in the day to do this OR we make a tradeoff and cut corners or settle for “good enough” in order to take on multiple items at once.

So this year we’re setting ourselves up to be successful. We’re going to say “yes” a lot less and “no” a lot more. It’s about recognizing the trade-offs. It’s about understanding what each additional “yes” really means as it’s not as simple as adding one more thing to our list - it’s the opportunity cost of our time working on Task X vs Task Y. But more importantly, it’s about having EXTREME clarity in what THE most important + impactful thing is that we can be doing and focusing on just that thing. We’re all familiar with the Pareto Principle (80/20 rule). We know what 1-2 “unsexy” things drive 80% of the results we seek, yet we love to chase the shiny things that, while fun, aren’t anywhere near as impactful.

And once we have that clarity on what are THE most important/impactful things that we should be doing, we focus on those + set the expectation that these won’t just be done, but that they’ll be done at a 10/10 standard of quality.

10/10 standard of quality

6/10.

If I’m being honest with myself + the bar I hold for myself, that’s the score I’d give myself on average for what I executed upon last year.

It wasn’t for lack of effort. It goes back to the above point - I let my focus get pulled into so many different things that the things I wanted to do became items to cross off my checklist vs. things that needed to be done deeply and with excellence.

We used to be able to get away with this because 25 6/10 blog posts optimized for SEO took a fair bit of time to work through and was something that competitors may not be willing to commit resources to. So it was a growth differentiator. Fast forward to today’s world and we can get 25 blog posts optimized for SEO with just a few prompts into your LLM of choice and all you have to do is paste them into your CMS. (Note: please don’t do this, this is not me recommending that - just showing how easy it is to do nowadays)

So as we move into this age of AI, of new companies and products entering the market at a speed never seen before, mediocrity is only going to grow in volume. The returns we used to get from shipping something simply to get it shipped and out there are quickly going to consolidate down to near zero.

What this means for me is that if I’m going to do something, the requirement behind it is that I first ask myself, “What does a 10/10 version of this look like?” and then set that as the benchmark for what the final version of it needs to be. And this is exactly why it complements having dogged focus. We can’t 10/10 everything. We have to be selective about where we apply it. We have to choose what truly deserves to be executed at that level because the outcome of it should be a significant business result.

AKA, we have clarity on exactly what we need to do and the bar at which it needs to be done. From there, it’s simply keeping the discipline day in and day out to stay on the path. Nothing sexy. No silver bullets. No “hacks.” Not doing “more.”

Just executing.

Book quote of the week

“If you are trying to simultaneously execute a number of new goals, each of which requires a high degree of engagement to achieve, you will inevitably be frustrated by your results…Attempting to spread limited capacity across multiple goals is the most common cause for failure in execution.”
- The 4 Disciplines of Execution, from FranklinCovey

See you next Saturday,
Sam

I’ve gotten other variations of that question 25+ times since publishing that piece.

The problem isn’t understanding Dark SEO - it’s surviving the implementation + adaptation of it.

So Tim and Oliver from YOYABA asked if I’d join them for a masterclass on how to navigate this last week. Hundreds of marketers watched it as we went deep on the data, frameworks, + tactical shifts we’re seeing. (+ here’s the recording for anyone interested)

And the questions they asked revealed the real problem:

Although some are starting to understand Dark SEO conceptually, most have no idea how to operationalize it without losing their budget, their leadership’s trust, or their job.

This isn’t about what Dark SEO is (I covered that last month here). It’s about the 3 moments where your Dark SEO strategy dies before we even get it off the ground + how to survive those.

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Sponsor: HockeyStack

You just closed a $150k deal. The prospect had their badge scanned at an event, saw 94 ads, got 5 calls/emails from a BDR, and read 3 blog posts. Now the CEO asks: “Who gets credit for this deal?”

But what if I told you that isn’t the question we should be asking?

For years, this was the question I was trying to answer because for years I operated with the “additive” mindset. What happens if we hire 3 more BDRs? What happens if we add $15k more ad spend? And then I would simply map out the anticipated ROI of that effort through our funnel and add it to our current expected outcomes. Hence “additive.”

And then the lightbulb went off. We weren’t successful because of one of those specific channels. We were successful because of how we leveraged the interplay between them.

I’ve had multiple chats with Emir Atli at HockeyStack over the past year about this subject, and this is exactly what they’re helping marketers and GTM leaders solve for.

(Im)Prove marketing's value

Death Moment #1: The board meeting where you lose your SEO budget

Here’s how it happens:

The board asks: “What’s our ROI on SEO?”

You pull up your handy dandy dashboard: “Impressions are up 150%, we’re ranking for 47 new keywords, domain authority increased to...”

They interrupt: “Sam, how much revenue did that drive?”

You say: “Well, attribution gets tricky with organic search...”

(And this is where you lose the budget)

I’ve heard about this happening three times this past quarter. Different companies, but the same exact conversation + same outcome.

The problem: We’ve been answering with channel metrics when they want outcome metrics.

Here’s the exact fix

Stop reporting on “SEO performance” + start reporting on “organic impact on pipeline.”

Here’s what this looks like when asked about SEO/organic performance:

Bad answer
“We’re ranking #3 for ‘best ATS’ and getting 2,000 visits per month from it”

Good answer
“In Q4, 23% of our closed deals cited organic search in their buying journey. Brand search volume is up 48% since we started, indicating they were already familiar with us when coming to the search engine/LLM. That’s $12.34M in pipeline this quarter.”

What to show them:

1. Brand search volume trends (leading indicator of demand)

   • June: 6,600 searches

   • September: 8,100 searches (+23%)

2. Self-reported attribution (how many deals cite “web research,” “Google,” “ChatGPT,” etc.)

   • Track this in your demo form

   • Ask sales to note it in discovery calls/pull this from call recordings

3. Pipeline impacted from organic efforts

   • Use triangulation: CRM attribution + self-reported + sales call transcripts

   • Show the full journey, not just the last click

Here’s what an example of this looks like:

Instead of saying “organic traffic is up 12%!”

Say this: “Organic demos are up 42% QoQ. That translates to an increase of 126% in pipeline generated. And we had 17 deals won in September sourced specifically from LLMs.”

Same data. Different story.

One keeps your budget. The other kills it.

Why this works

Your board doesn’t care about impressions. They care about what drives revenue.

When you show pipeline + revenue influenced (not just last-click attributed), you’re speaking their language.

If you can’t connect your SEO work to pipeline/revenue in the next board meeting, your budget is at risk. It doesn’t matter how good your strategy is if you can’t communicate it in a way that they understand.

Death Moment #2: Your team revolts because “the metrics don’t make sense”

Here’s the scene:

You just came back from the masterclass, fired up about Dark SEO.

You tell your team: “We’re changing how we measure SEO success. Clicks don’t matter anymore. We’re tracking AI visibility, non-branded impressions, + brand search now.”

Your SEO manager says: “So... we’re not tracking rankings anymore?”

Your content manager says: “Wait, how do I prove my work is valuable if we’re not measuring traffic?”

Your demand gen manager says: “How will we have any idea what’s actually working then?”

(This is where your strategy dies from internal resistance)

Most leaders think the problem is getting team buy-in. It’s not.

Here’s the problem: You’re changing the metrics without changing the incentives.

Here’s what happens when you don’t fix this:

Your SEO manager keeps optimizing for rankings because that’s what they know how to do.

Your content manager keeps writing for pageviews because that’s how they justify their job.

Your demand gen manager keeps reporting MQLs because that’s what’s in their dashboard.

Six months later, you’re back in the board meeting. Same questions. Same awkward silence. Except now you’ve spent another quarter’s worth of budget + time on a strategy your team never actually implemented and your board is wondering if they’re taking crazy pills because nothing’s changed.

Here’s the exact fix

With it coming down to incentives, we can’t just change what we measure. We have to change what we reward. This needs to be done via the conversations had with your team.

“Here’s what’s changing + here’s why it matters to you.”

To your SEO manager

Old way:
“You’re measured on rankings + traffic. Success is ranking #1 in the SERP + driving more traffic to the site month-over-month.”

New way
“You’re measured on AI visibility, non-branded impressions, + brand search lift. This is better for you because when brand search goes up, leadership sees the direct correlation to pipeline. That makes your work more valuable, not less. Rankings that don’t drive brand recall = busy work. Visibility that drives brand search = revenue impact.”

To your content lead

Old way:
“You’re measured on pageviews + time on site”

New way:
“You’re measured on citability + findability. Here’s the new question: ‘When prospects compare solutions, does our content show up?’ We’re tracking: 1) How often we appear in AI Overviews for comparison queries, 2) How often sales hears ‘I saw your content about X’ in disco calls, + 3) Self-reported attribution citing ‘web research.’ Every piece of content gets audited: Did it influence a deal? If yes, that’s a win. If no, we learn + adjust.”

To your demand gen manager

Old way:
“You’re measured on MQLs from organic search”

New way:
“You’re measured on pipeline from organic. We’re not giving up on attribution. We’re expanding it. The old way was solely based on last-click/first-click attribution. The new way is triangulation across CRM data + self-reported + sales intelligence. Your job got more important, not less. You’re now connecting the dots that most attribution tools miss.”

Pro tip: Tie the new metrics to their performance/career advancement. (This is the type of tactical item that fits perfectly into a performance assessment that’s actually helpful)

Show them how measuring Dark SEO correctly makes their work more visible to leadership, not less.

Why this works

People resist change, especially when they think it hurts them (AKA, they don’t understand why the change is occurring). They embrace change when they see it helps them.

If your team doesn’t understand how the new metrics make their work more valuable, they’ll never be bought in + the new strategy will die before it makes it off the ground. They’ll keep optimizing for the old metrics + your Dark SEO efforts will be for nothing.

Death Moment #3: You published 47 blog posts + none of them drive pipeline

Here’s what’s happening right now at most B2B companies:

The content team publishes 20 blog posts per month. The marketing leader asks: “How’s content performing?”

Data shows things like:

• 50K pageviews this month

• Average time on page 2:43

• Bounce rate 67%

So the marketing leader thinks: “Love it, the content is working.”

Three months later

The marketing leader is sitting in their quarterly business review with leadership/their board. The CFO asks: “What’s our ROI on content?”

So the marketing leader pulls up that data + reads it out, leading to the inevitable question from the CFO that we’ve all been asked a million times: “How many deals did content influence?”

(This is where content becomes viewed as a cost center vs. a revenue driver)

Here’s the problem: We’re measuring output (posts published) instead of outcome (deals impacted).

Here’s the exact fix

Audit your content for findability + citability.

Stop asking: “How many posts did we publish?”
Start asking: “How many deals did our content influence?”

The 10-deal audit:

Pull your last 10 closed deals (won AND lost).

For each deal, ask yourself:

1. “Did any of our content come up in the buying process?”

2. “Did the prospect mention anything they read or researched?”

3. “What did they say when asked ‘how did you hear about us?’”

Note: these can be done with tools like HockeyStack OR through good old fashioned research. Leverage. your self-reported attribution data like in #3. Listen to call recordings to see if they were mentioned. Grab a few AEs and ask them directly. Reference first + last touch data captured by your marketing automation tool. Etc.

If the answer is “none” or “I don’t know” for all 10 deals re: if content was involved, your content is NOT working. It doesn’t matter how much you publish, volume isn’t the issue.

If the answer is “yes” for 3+ deals, find the pattern. What content showed up? Where? When in the journey? What was the topic? What medium(s) were they in? What channel(s) were they consumed on?

Real example from our audit:

I did this exercise this year. Grabbed 10 deals to review. 7 of them cited content.

But here’s what we learned:

• None of them cited the standard “fluffy SEO” posts (500+ word, keyword-stuffed garbage targeting a super high-volume keyword)

• All 7 cited either: 1) Podcast episodes we’d transcribed, 2) Comparison posts (”X vs Y”), or 3) Deep expertise content (our ABP playbook)

The fix we made:

We stopped using the “standard” SEO playbook + instead doubled down on:

• Transcribing every podcast episode (make it AI-readable) + also turning those into their own unique blog posts based on the topic

• Writing comparison content (what prospects actually search)

• Creating expertise content (what makes us different)

The results:

Published something like 25% fewer posts (that no one enjoyed writing anyway). Influenced 2x more deals.

The tactical checklist

For every piece of content, we now ask:

Findability:

• Does this answer a question prospects actually ask?

• Can AI extract a clear answer from this?

• Does this show up when prospects compare solutions?

Citability:

• Is this quotable? (Or is it generic fluff?)

• Does this include specific frameworks/methodologies?

• Would a prospect remember this 2 weeks later?

If the answer to any of these is “no,” don’t publish it. It’s better to publish 5 pieces that influence deals than 20 pieces that don’t make meaningful impact except drive pageviews.

Why this works

Content that gets published ≠ content that gets remembered.

In the Dark SEO era, we’re not optimizing for clicks. We’re optimizing for mental real estate.

If our content isn’t showing up in sales conversations, it’s not working. It doesn’t matter how “optimized” it is.

The CEO questions (+ how to answer them)

You’ve survived the 3 death moments…
…but your CEO still has questions.

Here are the questions you should anticipate + how to respond:

Question #1: “If AI answers everything, why are we still doing SEO? Should we shift budget to paid?”

Bad answer
“SEO is a long-term play. We need to be patient.”

Good answer
“SEO is a down payment on making paid more efficient. Here’s the math:

When someone sees us in an AI Overview but doesn’t click, they file our name away. Then when they see our ad 2 days later, we’re not cold/unknown anymore. They’re familiar with our name and have at least an idea of what we do/the problem we solve.

For example, without organic visibility, our paid numbers look like:

• Paid ads = $487 CAC

• 3.2% conversion rate

But with high organic visibility, they look like this:

• Paid ads = $213 CAC

• 7.8% conversion rate

SEO isn’t competing with paid. It’s making paid more effective.”

Q2: “What’s the point of ranking if nobody clicks anymore?”

Bad answer
“People will eventually click.”

Good answer
“Ranking ≠ clicks. Ranking = mental real estate.

When someone searches ‘best ATS for agencies’ + sees us in the AI Overview, they’re not clicking. But they’re filing our name away.

Then when they’re ready to evaluate, they search for US directly.

We’re literally seeing this play out in real-time:

• Unbranded clicks: flat

• Brand searches: +23%

• Demos from branded searches: +42%

That’s not failure. This is exactly what we saw with dark social in 2020 + it’s the same exact pattern now with dark SEO.”

Q3: “How do I explain declining traffic to the board when competitors are growing?”

Bad answer
“Traffic doesn’t matter anymore.”

Good answer
“Traffic’s correlation to pipeline/revenue growth has gone from a strong, positive correlation to a correlation closer to 0. It’s not bad, but it’s not what it once was as an indicator of future growth.

If our traffic is down but our pipeline from organic is up 2x, that means we’re showing up in higher-intent searches.

Competitors might have more traffic because they’re ranking for fluff keywords that don’t drive pipeline (AKA, what we used to do and then wonder why all that traffic we had wasn’t turning into pipeline).

We’re ranking for comparison queries + AI citations that drive direct brand searches.

I’d rather have 1,000 visitors who convert at 8% than 10,000 visitors who convert at 0.3%.”

What to do if you actually want this to work

Most people will read this + nod along…but change nothing.

If you want to survive these 3 death moments + conversations with your CEO/board, do this:

The first week back in January

1. Audit your last board deck

Did you show channel metrics or outcome metrics? Can you connect your organic work to pipeline + revenue? If not, rewrite it before the next meeting.

2. Have the metrics conversation with your team

Don’t just announce new metrics, explain how the new metrics make their work more valuable + tie it to their career advancement.

3. Run the 10-deal content audit

Pull your last 10 closed deals + look into them, asking yourself “Did our content come up?” Then find the pattern, kill what’s not working, + expand on what is.

By the end of January

Audit your top 10 “money keywords” - the searches that matter most to your business.

If you don’t know what they are, ask sales “What do prospects say they searched for before finding us?”, look at your CRM data for patterns in how people discovered you, and/or listen to call recordings.

Once you have your list, search for each one in:

• Google (SERP listings)

• Google (AI overviews)

• LLMs (ChatGPT, Claude, Perplexity, Gemini, etc.)

As you go through each one, ask:

1. Does our brand show up? (yes/no)

2. If so, how is it positioned? (1st, 2nd, 3rd, not mentioned, etc.)

3. What’s the sentiment? (positive, neutral, negative)

4. Sources cited (our website, 3rd party review site, competitor’s comparison page, etc.)

Put it in a spreadsheet. This becomes your baseline. If you’re not showing up in at least 2 of those 4 places for your money keywords, this isn’t a traffic problem, it’s a findability problem. Fix that before you worry about anything else.

Wrapping up: the gap between knowing + doing

Most marketers are starting to understand Dark SEO. They’ve seen it before with Dark Social and are using that as their mental model.

So the challenge isn’t what to do, it’s how to do it when:

• Your board still wants click-based ROI

• Your team is still measured on the old metrics

• Your content isn’t built for AI citability

This is the gap between knowing what to do + actually doing the work for this to be successful.

The 3 death moments

1. The board meeting where you lose your budget

2. Your team quietly sabotages the strategy

3. You publish 47 posts that drive zero pipeline

Most teams will hit all three during 2026, + most won’t survive.

The gap isn’t understanding Dark SEO. It’s implementing it when your board wants clicks, your team wants traffic, and your content is built for Google circa 2019.

The teams that survive aren’t the ones who understand Dark SEO first. They’re the ones who operationalize it while everyone else is still explaining what it is.

Book quote of the week

“Never take it for granted that your past successes will continue into the future. Actually, your past successes are your biggest obstacle: every battle, every war, is different, and you cannot assume that what worked before will work today.”
- The 33 Strategies of War, by Robert Greene

See you next Saturday,
Sam

P.S This is part 7 of my SEO series as I share in real-time what I’m learning + what we’re seeing as we continue to push harder into the world of SEO here at Loxo. In case you missed the earlier editions:
Part 1: SEO isn’t dead
Part 2: They told me “no”
Part 3: “Is it working?”
Part 4: The “Alligator Effect”
Part 5: We cut our best keywords
Part 6: Dark SEO

And if you’re like most people, you’re about to open a document that looks something like this:

“Communicates effectively”
“Works well with others”
“Drives results”
“Shows initiative”
“Demonstrates leadership qualities”

You rate yourself 1-5. Your manager rates you 1-5. Maybe there’s even an open text field to leave a vague comment about the vague criteria.

As a manager, these assessments are traditionally very time-consuming and often dreaded as we try not to view them as a waste of time.

As the receiver, these assessments are traditionally looked forward to as the one time a year to get direct feedback and have a career conversation…but most of the feedback we seek and the path charted for career progression aren’t included in the assessments.

This feedback loop is broken.

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Sponsor: Redpoint Insights

Ever wonder why so many “research-backed” reports fall flat? It’s because no one owns the process end-to-end.

Content marketing agencies are great at writing, but most don’t have deep survey design expertise. So they lean on clients for help with the questionnaire…or outsource pieces of the research…or hope the data will magically produce a strong narrative.

On the other side, market research firms know how to run surveys, but they don’t know how to turn data into a compelling, revenue-driving story. They deliver statistically correct findings — but not the angles, headlines, or narrative tension that make buyers care.

And when research and content don’t work together from the start, the report ends up weaker than it should be.

Automox lived this before coming to Redpoint Insights. Their previous content agency leaned heavily on Automox to help write the survey. The final report looked fine, but the data wasn’t strong enough to drive PR, demand gen, or sales conversations.

So they switched to Redpoint Insights + tripled their leads in a single month after launching their new report compared to an entire year with their previous report from their previous agency.

Redpoint solves the gap by doing what most firms can’t: They bring market research rigor and content strategy expertise together so every insight is engineered to drive narrative, authority, and pipeline.

If your 2026 plan includes publishing research that doesn’t just look good — but actually drives revenue — let’s talk.

Book a research strategy call

Generic assessments are broken

Here’s the thing about the stock assessment frameworks we’ve all had to use at some point or another over our careers: they’re not broken because someone designed them poorly, they’re broken because they’re designed to be universal.

And as we well know when it comes to marketing copy and sales talk tracks, universal = irrelevant. When something is designed for everyone, it’s designed for no one.

“Communicates effectively”
Super vague. What does that mean? Does it mean you’re clear in meetings? Does it mean you write well? Does it mean you influence people? Does it mean you listen? All of the above? None of the above?

“Works well with others”
Awesome, you are a functioning member of society, congratulations. But what does that actually look like in your role? With your team? With leadership? With the market?

“Drives results”
Always love this one. A criteria that is probably the most weighted when it comes to getting a raise (or being put on a performance improvement plan (PIP)), but zero context as to what “results” actually mean.

The problem ultimately comes down to 3 things:

1. They’re not specific
   They lack the clarity that actually drives improvement. You can’t improve on something that’s ambiguous.

2. They’re too opinion-based
   This should be an objective, not subjective, evaluation. “You’re good at communicating” is subjective. “You communicate strategy, priorities, and reasoning with simplicity and clarity” is objective - it’s observable + measurable.

3. They offer no direction
   Generic assessments tell you what you’re doing. Tailored assessments tell you where you need to go. Think: a mirror vs. a map.

At the end of the day, the ironic part about this is that both take about the same amount of time to fill out. Why waste the time on something that doesn’t help us actually improve?

Tailored > generic assessments

Here’s the “aha” I had this week:

Vague feedback provides no roadmap
Roadmap requires specificity
Specificity creates clarity
Clarity creates growth

A custom assessment does something a generic one never will. It gives you + your manager a shared definition of what success actually looks like in your specific role, with your specific context, at your specific company, for your specific growth.

Instead of wondering “am I good at leadership?” you know exactly what you’re being assessed on:

• Do you translate company vision into actionable direction?

• Do you identify underperformance early?

• Do you develop talent?

• Do you operate as a force multiplier?

Each one is specific, observable, + tells you exactly what to improve.

And here’s the best part: this also makes it 10x easier for your manager. They aren’t trying to interpret what “communication” means in your role. They have a clear rubric + can assess you objectively instead of subjectively.

This is where the magic of these custom assessments happens. When both people are looking at the same definition of success, suddenly the assessment becomes useful. It becomes a growth tool instead of a compliance exercise or a box checked as something that has to be done every year.

So how do we build one?

The three-part framework

Component 1: your job description

Start with your actual job description. Not just the one you had when you applied. But also add in the items that reflect what you actually do in your day-to-day today.

What are you accountable for? What are the 3-5 outcomes you’re measured on? What does success look like in your role?

For example, in my role as a marketing leader ehre, my actual job description looks like:

• Build + lead a high-performing marketing team

• Own marketing strategy + execution

• Drive pipeline + revenue impact

• Establish Loxo as a market leader

• Ensure cross-functional alignment across GTM

So why include items like these in your assessment? Because it anchors everything to reality. It grounds the assessment in what actually matters (according to what you were hired to do). Not generic competencies or abstract traits, but what you’re specifically accountable for.

Component 2: company values + traits

Every company has values + traits that make them who they are. Sometimes they’re written down. Sometimes they’re plastered on the wall in a super tacky poster. Sometimes they’re modeled by the behavior of the individuals already working there.

At Loxo, our values include things like: being a simplifier not a complicator, possessing high agency, long-term thinking, having an ownership mentality, + constantly seeking 1% improvements.

These should be included in your assessment because they define how you’re expected to do your job, not just what you do.

For my assessment, I included things like:

• “Models the behaviors, standards, and expectations that set the tone for both the marketing + larger organization. Creates a high-performance culture through example.”

• “Identifies mediocre standards or underperformance early and raises the bar through coaching, clarity, or structural changes”

• “Communicates strategy, priorities, and reasoning with simplicity + clarity”

• “Converts feedback, data, or failure into measurable behavioral improvements”

Why include these?

Because as the old saying goes, “Culture doesn’t happen by accident.” It happens when our assessments - the thing we’re being evaluated on - reinforce the values we are supposed to care about + strive toward. This ensures that how you operate aligns with who you are as an organization.

Component 3: specific competencies (strengths + weaknesses)

This is where you get granular. What are the specific competencies that matter most for your role?

And for each competency, what does it actually look like?

Don’t just write “Leadership.” Break it down:

• “Understands the company vision, translates it into actionable direction, and communicates it clearly to team members“

• “Models the behaviors, standards, and expectations that set the tone for both the marketing + larger organization. Creates a high-performance culture through example.“

• “Takes responsibility when outcomes fall short and gives credit generously when the team succeeds“

• “Sets clear priorities, roles, and success metrics so team members always know what great looks like“

• “Maintains calm and composure during high pressure or uncertainty, providing stability for the team“

For each of those sub-items, you then define what “Basic,” “Intermediate,” and “Advanced” actually means.

Do this for your areas of strength. Do this for your areas of weakness.

Where do you need to continue to keep the pedal down to make the most of your strengths? Where do you want/need to improve? What does that competency look like broken down?

Why include this section?

Because it forces both you and your manager to get specific about what matters. You’re not vaguely “working on leadership.” You’re specifically working on “translating company vision into actionable direction” or “identifying underperformance early.”

That specificity is what creates growth.

How I built mine (+ how you can build yours)

When I sat down to build my assessment, I started with a question: What do I actually need in order to be successful in my role?

Not “what does a VP of Marketing typically need?” But what do I need to be excellent at here, now + at my company.

So I pulled my job description. I listed out what I’m actually responsible for. Then I looked at our company values. Which values/traits need to show up in how I work Then I listed out my focus competencies. For each one, I asked: what does excellence require?

And I got specific.

Instead of writing “Communication,” I wrote:

• “Communicates strategy, priorities, and reasoning with simplicity + clarity”

• “Ability to clearly communicate business outcomes resulting from marketing + GTM efforts”

• “Manages and resolves conflicts and disagreements in a constructive manner”

• “Manages up effectively and sets expectations clearly”

Each one is different. Each one is specific to my role. Each one tells me exactly what I need to work on.

Then I looked at my growth areas. Where do I want to improve to get us to the next level?

Strategic judgment and decision-making is a competency area for me here. So I listed out criteria like:

• “Presents recommendations with clear reasoning, alternatives considered, and expected results”

• ”Prioritizes the right items relative to business needs and market opportunities”

• ”Anticipates risks, opportunity costs, second-order effects, and mitigation paths”

• ”Demonstrates high clarity in ambiguous or rapidly changing environments”

• ”Makes decisions that strengthen the company long-term, not just in-quarter”

Now I have something to actually improve on. Not a vague sense of “I need to be a better decision-maker.” I know exactly what that means.

Then I included the scoring mechanism. This is the MOST important item to define ahead of time for both parties. What is the scoring system. What does each “score” mean? What does the higher level score look like compared to my current “score”?

For my manager, I even noted this for him at the very top of the assessment:

Reminder: this is for growth + coaching, to point out areas I am excelling in + should maintain, and areas I am weak in + should seek to improve. “Basic” here at Loxo = “Advanced” at most any other company.

An assessment that has us overinflated at “Advanced” in nearly everything isn’t helpful. Yeah, it feels good for the ego, but it gives a false sense of mastery + results in turning down the growth dial in yourself that got you to where you are.

I like to use this in context of two things for my direct reports:

1. How are you performing relative to this criteria + the position/seniority you’re in today?

2. Based on what I know of your upside here + what you’re capable of, if there’s extensive room for growth ahead in this area, I know you’re far from what would be “Advanced” for you.

And the beautiful thing is that this framework works at every level.

Moving away from my assessment to our Organic Growth Marketing Manager’s - we have some of the same overarching competencies (communication, growth mindset, etc.), BUT, the specific skill/behaviors listed as part of it are different - they’re tailored to that individual.

Then we also have competencies that are specific to their job description, like

• SEO ownership (technical, on-page, off-page)

• Organic growth strategy and execution

• Cross-channel organic visibility (SEO + AEO + YouTube SEO + Reddit, etc.)

And the competencies reflect that. They’re specific to organic growth, not general marketing.

But the structure, the thinking, + the specificity are the same.

That’s the beauty of this framework - it scales. It works for individual contributors. It works for managers. It works across different departments.

Because it starts with what actually matters in this specific role, in this specific company, for this specific person?

Not: “what generic assessment template can we apply for every employee at our company?”

The template

I’ve created a template you can use to build your own assessment. It has placeholders for:

• Your job description items

• Company values/traits that matter

• Your core competencies (strengths to maintain)

• Your growth areas

It only takes 1-2 hours to fill this out. Do this today while you’re enjoying your cup of coffee. Or do it early next week so you can share it with your manager to include in your assessment.

Because here’s the thing: your manager probably definitely isn’t going to build this for you. If you want a custom assessment, you have to take the initiative.

The template:

You can use it TODAY. It has four sections:

1. Core job description competencies
   3-5 items based on what you’re actually accountable for

2. Core company trait competencies
   3-5 items based on your company values + how you need to operate

3. Core strength/weakness competencies
   3-5 items you’re excelling at + 3-5 areas you need to develop

4. Growth + reflection
   Retrospective on the past few quarters + some forward-looking goals to document and align on

For each competency, you fill in the definition, then break down 4 specific sub-items. Then you define what Basic/Intermediate/Advanced looks like.

It takes 1-2 hours to fill out. That’s it.

Access the template here: (don’t worry, it’s free) https://docs.google.com/spreadsheets/d/1EaK4OarYZPOSHesvvnsIye3RdV-HxDuqlXOz2nBHT5A/edit?usp=sharing

Fill in the placeholders. Make it specific to your role. Make it specific to your company. Make it specific to you.

Then give it to your manager and say: “I built this custom assessment because I think it’ll be more helpful for both of us. I’d like to use this for my review.”

Your manager will be impressed. They’re going to see that you’re taking ownership of your own growth. They’re going to have something actually useful to work with. And they’re going to put that much more thought + feedback into it knowing how important + valuable it is to you.

TL;DR (even though you did read all the way to this point)

Annual review season doesn’t have to suck. It doesn’t have to be a checkbox compliance exercise. It doesn’t have to be a vague conversation about generic competencies.

It can be a growth tool, but only if you’re willing to take ownership of it.

Generic assessments are a waste of everyone’s time. They’re vague. They’re opinion-based. They don’t provide direction on how to actually improve.

Custom assessments are specific. They’re measurable. They drive growth.

Custom assessments take a little more time up front to build out, but the ensuing conversation + path laid out are worth 100x the hours spent creating it.

So this week, don’t wait for your manager to send you a stock assessment template. Go build your own + get specific with it. Then give it to your manager.

Your future self will thank you.

Book quote of the week

“And if I’ve faied, it’s no one’s fault but mine. Because I didn’t pay attention to what they told me - to what they taught me, practically, step by step.”
- Meditations, by Marcus Aurelius

See you next Saturday,
Sam

Who needs coffee in the morning when you can start your morning reading a message that opens with the above sentence?

This past week I had not 1, but 2 failures lessons learned. And I’m sharing these here because 1) selfishly, these essays are for me at the end of the day to reflect on what I see and observe and 2) to reiterate that marketing and growth in general isn’t always pretty - no one bats 1000, and that the learnings come just as much, if not more, from what didn’t work.

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Sponsor: HockeyStack

You just closed a $150k deal. The prospect had their badge scanned at an event, saw 94 ads, got 5 calls/emails from a BDR, and read 3 blog posts. Now the CEO asks: “Who gets credit for this deal?”

But what if I told you that isn’t the question we should be asking?

For years, this was the question I was trying to answer because for years I operated with the “additive” mindset. What happens if we hire 3 more BDRs? What happens if we add $15k more ad spend? And then I would simply map out the anticipated ROI of that effort through our funnel and add it to our current expected outcomes. Hence “additive.”

And then the lightbulb went off. We weren’t successful because of one of those specific channels. We were successful because of how we leveraged the interplay between them.

I’ve had multiple chats with Emir Atli at HockeyStack over the past year about this subject, and this is exactly what they’re helping marketers and GTM leaders solve for.

(Im)Prove marketing's value

Feedback loops + ego checks

Whenever I see results or get feedback that something didn’t go to plan, my immediate reaction is to want to hide from it, to pretend it didn’t happen, and move on.

Unfortunately, whether it be marketing or any growth-oriented endeavor, very few things are ever one-and-done activities. They’re most always things that are done consistently over time.

Multiple ad campaigns over the course of a year
A multi-step email nurture sequence
An ongoing educational webinar series

Or in the case we opened this newsletter with, local micro-events.

Knowing that we’re just starting to get these micro-events off the ground + that they’re going to be a big part of our marketing plan for the upcoming year, my head went to these two quotes, which sum up my options for how to move forward better than I could have said myself:

• “Insanity is doing the same thing over and over again and expecting different results.”

• ”Learning is applying a new behavior under the same condition.”

This is where we need to let the feedback loop serve its purpose - letting us know that something’s not right, that if we do the same thing again, that we’re going to get the same (poor) outcome.

And this is the ego check part. This is where we need to be ok saying, “I don’t have it all figured out, but I know this isn’t it.” Then we come up with the next variation for how we want to approach it. Or to the above quote’s point - applying a new behavior and seeing how that affects the outcome.

Lesson 1 - local micro-events

“I want to be completely transparent, last night’s event in my opinion was a complete disaster.”

Local micro-events are going to be a big part of our 2026 plan. Early December is the recruiters’ slow season as they’re learning, networking, + preparing for the new year - AKA the perfect time to host an event where they can do exactly that.

We had one this past week. And that opening quote was the start of the feedback I got the next morning.

When I received it, I had two options:

1. Let my ego defend what happened, or

2. Take it as a learning mechanism and make sure it never happens again.

Option 1 is easy. Option 2 is hard. But that’s growth. So I braced myself, knowing the feedback was necessary.

What actually happened

I was optimistic about this event. Looking back, I was too optimistic/confident. I’d stepped back from planning when I should have leaned in.

We booked a venue downtown with the expectation of a private, exclusive space for networking. Here’s what attendees actually found when they arrived:

We had 3 tables in a busy bar. There was zero privacy as the tables were surrounded by other parties.

Other groups had ice buckets, full setups, and proper branding. We had nothing until a member of our team specifically asked for it.

And by 8pm, it had turned into a nightclub bar.

We’d invited 1-2 people per company - a decision that would end up haunting me. When the first attendees walked in, one asked: “Are we the only ones here?”

Yes. Because people don’t show up to these things alone, especially after a long day. That’s not on them. That’s on us for not thinking through the psychology of attendance. They’re much more likely to come if they have colleagues to share the experience with vs. going solo to a bar event.

When we debriefed with the venue, the story became clear. They told us our booking was “too small for a private section” because of the number of people we’d originally confirmed. And there lay the disconnect. Somewhere between our internal expectation, what we communicated to the venue, and what they understood, things got lost.

But here’s what gave me the most anxiety after getting this feedback - if the invitees from our strategic account list (prospect or customer) had shown up, this would have been a disaster. Not just logistically. Strategically.

We position ourselves as a premium brand. And we just hosted an event in the middle of a bar with no signage or privacy.

The lessons learned

Here’s what I didn’t do that I should have (and will in the future):

Expectation alignment with the venue: I assumed we had the same definition of “exclusive, high-end event space.” I thought “private/walled-off room.” They heard “communal bar area.” I should have gotten into the weeds and been explicit.

Invite strategy: I didn’t think deeply enough through who we invite or why. We scattered invites across companies assuming senior leaders would show up solo to a bar after work. They didn’t. Next time: invite groups from our top target companies. Make it feel exclusive and coordinated.

Execution perception: Every detail from the space, the setup, the signage, the drinks, and more sends a signal about who we are. This was a tough one for me to swallow as reflecting back on it, the signal for this event was significantly under our bar of acceptance. But the market doesn’t know that.

Ownership: The buck stops with me. I didn’t involve myself enough in planning and execution. And if we’re serious about running high-end events that reflect our brand, the resourcing + execution for these need to be leveled up ASAP.

And on that note - these events aren’t exclusive to marketing performance solely. Customers are involved. Prospects are involved. That means Sales and Customer Success are impacted by this.

The same morning I received the feedback about the event, I sent the exact initial feedback I received to our senior leadership group on Slack + an accompanying message. I don’t want them to be surprised and hear this from others before me. And I want them to know what we’re doing about it from here:

“Following up on the event yesterday with this group. The tldr from internal feedback on the event was that it was a flop. below is [redacted]’s feedback that lays it all out for this group to see in full transparency.
I’m gathering all feedback from the event this am + will follow up next week with a proper post mortem on all of this so we can course correct for 2026 ASAP. I own this miss entirely and will make sure this never happens again by inserting myself significantly more into the planning + execution of these until they’re operating at our Loxo expectation bar.”

These are tough + uncomfortable questions to ask and answer, but they’re important if we want to LEARN from the experience so we can improve the next time around.

Lesson 2 - communicating with execs

Marketers love words. They’re part of why most of us reading this love (or hate) our vocation. The creativity we’re given to express who we are, what we do, the feelings we want to evoke, the connotations we want implied by the words we choose, etc.

But with this love of words comes another very important responsibility - defining those words and making sure that all involved in the conversation understand the explicit meaning of each of them.

…and I had a fun reminder of this exact lesson this past week with our CEO.

This is a lesson I’ve learned before - and not just once either. It seems to be one of those recurring lessons that emphasizes the importance of proactively getting ahead of communications with any receivers, but especially execs.

Case in point: some recent messaging + positioning work

As AI has entered just about every market + industry this year, we wanted to come up with a better/stronger POV around it vs. just saying we’re yet another “AI-Powered [category] software”.

Months were spent working through different options, angles, enemies, frames, positions, and more and we landed on one we really liked that could truly stand on its own not just now with the AI craze, but as time goes on as well as an evergreen position.

The first 95% of the meeting was incredible. The team was speaking brilliantly to the insight uncovered, how we saw things playing out, how it compared to the market, what it meant for our marketing, etc.

Then the words “company positioning” came up. That this would be something that would cascade beyond marketing + to all internal team members so everyone was speaking the same language. But when our CEO heard “company positioning,” he had a different definition that operates by (rightfully so).

I made the critical mistake of not taking the time to better define the above and the conversation immediately shifted to not wanting to alter things product/market fit, etc.

We absolutely had no intent of shifting anything at that level, but the mistake had been made. I had accidentally allowed worry and concern in his mind to enter the conversation due to not being explicit in what we meant. And the last 5% of the meeting had a very different tone and feeling as a result.

This led to a few hours of clean up after the meeting ended to explain to him what we were (and weren’t) doing to put him at ease. And then a separate call with the other team members who were a part of the presentation to debrief on what went well, why things shifted during that last 5% of the meeting, and where things were at after talking to our CEO. A lot of time, energy, and enthusiasm went into this + it was critical not to let that momentum slip because of a lesson that I already knew but didn’t act upon appropriately.

Lesson learned (again).

Takeaway

Both of these failures had the same root cause: I assumed clarity in communication existed when it clearly didn’t.

With the event, I assumed I communicated expectations properly to our team + that the venue understood our standards as part of this. With the conversation with our CEO, I assumed we were using the same definition of “company positioning” relative to the meeting agenda.

Assumptions are expensive when trying to amend after the fact, but cost just a few minutes of prep/groundwork when done ahead of time. It’s much better to spend those few minutes up front to get everyone on the same page, even if I think everyone is operating under the same set of expectations/definitions. Our future self will thank us.

Book quote of the week

“Essentialism is not about how to get more things done; it’s about how to get the right things done…It is about making the wisest possible investment of your time and energy in order to operate at our highest point of contribution by doing only what is essential.”
- Essentialism, by Greg McKeown

See you next Saturday,
Sam