For the last two years, I’ve written something each November on about annual planning (side note: how has 2+ years already gone by??).
In 2024 I did a two-part series where part 1 covered reviewing the previous year + upcoming year’s goals and then part 2 covered how to set goals + craft your plan.
In 2025 I took an unstructured approach + braindumped all my raw thoughts on annual planning, mostly the stuff that leaders usually aren’t saying out loud.
Looking back on these, it’s interesting to see how my own thinking has evolved in just a few short years - what parts I still do, what I stopped doing, what I’ve added, and more generally just how I approach the whole task of annual planning. Especially in the beginning of this year when I was struggling to figure out how to hit growth goals while at Loxo without defaulting to the “more” bucket.
So as I’ve started getting questions from clients + peers on how to think about 2027 planning, here’s how I would approach it if I were in charge of coming up with the marketing plan:
Heads up - this newsletter’s going to be a long one, but I promise it’ll be worth every minute of reading. For those who want the abbreviated version, I’m giving you:
A sheet you can copy to diagnose your own funnel to figure out if you want to do it yourself
A special offer where I’ll come in + do the audit with you, showing you what your constraints are, what that’s costing you in pipeline + revenue, and how to fix them so you can hit your 2027 targets without having to rely on the “more” bucket
Sponsor: Primer
Performance marketing is having a moment. Outbound is broken. AEO is eating into SEO. But your buyers’ attention hasn’t left paid channels - the challenge is reaching the right people beyond LinkedIn and branded search.
Primer solves two of B2B advertising’s biggest pain points:
Effective targeting across Meta, Instagram, YouTube, Google, Bing, Reddit, LinkedIn, and more
Actionable insights that help you learn, refine, and continuously improve your campaigns
The result is a paid acquisition loop that gets smarter with every campaign.
It’s free to create an account, with unlimited website visitor de-anonymization and a free 30-day trial of Primer’s paid plans.
Step 1: baseline your current funnel
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 in life, 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 submitted
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 if you want to follow along - 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
STOP HERE.
Most marketers (myself included for years) will jump straight from this sheet to then playing with the “levers that we can control.” This is the right instinct, BUT, before assuming we’ll be able to improve them because we need to model out how to hit next year’s target via Wishful Target Forecasting™ (or what I’ve come to abbreviate as WTF when reviewing these), we need to stop and figure out WHY those levers are lower than they should be and WHAT the issue is that’s causing the constraint.
This leads us to step 2…
Step 2: diagnose your constraint(s)
Now that we have our historical data, we’re ready to identify which of the 4 common funnel constraints 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
Let’s go from theory to practice real quick
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?
Where is your mind immediately going to??
Here’s the order I would tackle it in:
Demo → SQO rate (marketing/sales alignment)
We can insert common fixes quickly here (prospect schedule meeting, fix internal data syncing, kickoff better marketing/sales alignment)
Demo quality/volume (lead gen 101 or broad targeting)
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
Win rate (product/market fit mismatch)
A result of the above + the length of their sales cycle
Annual contract value
This one + #5 shouldn’t be done UNTIL the first 3 above have been addressed
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
Variable marketing spend
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.
What I’ve learned after doing this for years
Here’s how this usually plays out after having watched it from different seats over the years.
Your 2027 plan will (probably) get approved in December, locking in the next 12 months of spend + headcount, as well as the pipeline/revenue target built from this year’s performance + bumping the numbers up in a forecasting spreadsheet to show finance how you’ll achieve them (aka WTF™).
It’s how we’ve done annual planning for years, so everyone will nod + agree.
But what I’ve come to realize over the past year especially is that the funnel constraint is rarely diagnosed when the plan gets built, it’s just accepted as part of the business and we cross our fingers that we can bump it up a few points.
Then January comes along + you start shipping spend + resources at the new, higher level. “It takes time for pipeline to build + then close” is what we tell ourselves as Q1 progresses. As we near the end of March + we look at how the funnel is playing out relative to what we forecasted, we have our first ohhh shit moment when we see our actual numbers coming up short of our optimistically forecasted numbers.
The most common constraint of the four that I’ve seen over time (a low demo → SQO rate) is also the cheapest/easiest to fix. A quick calendar scheduling tool + a week spent with sales ops to get routing rules in place + all of a sudden pipeline has doubled simply because more prospects are showing up for the disco/demo calls. That’s just one example of fixing the constraint vs. dumping more money in at the top and trying to brute force your way to a target.
Do it yourself, or do it with me
You have everything you need above to run this audit. Simply copy this sheet + follow the steps above yourself.
If you’re a marketing leader, I strongly recommend doing this yourself so you have your finger on the pulse of exactly how your system is running today.
If you’re a marketing practitioner, I strongly recommend you do as much of this exercise as you can so you can 1) get a sense for the bigger marketing system you’re a part of and 2) so you can then share it with your marketing leader + help them as they work through their 2027 plan.
If you’re a CEO, exec, sales leader, PE/VC partner, etc., send this to your team + have them go through it.
But if you’re unsure of how/where to get started, want an unbiased third-party’s assessment, and/or don’t have the time/confidence to do this, I can help you.
As a reader of this newsletter, you’re getting early access to a special annual planning offer that I’ll be announcing more broadly next week.
What is it?
A 2027 funnel audit + planning diagnostic
How does it work?
You send me your trailing 12 months of funnel data. Within 14 days, you get:
→ A one-page map of your constraint(s)
→ The gap benchmarked against 100+ funnels I’ve audited, in terms of pipeline + revenue
→ A prioritized fix plan + a “what to put in the 2027 plan” page
→ 3-5 board-ready slides + a recorded walkthrough
How much does it cost?
$5,000
I’ll be doing 10 audits total, with a last start date of Dec 1 (because we need these before 2027 kicks off…). Every audit starts with a 20-30 minute call between us to make sure it’s a fit (AKA you’re in B2B, sales-led, are $5M+ in revenue, have 12 months of CRM data, etc.). If it isn’t, I’ll tell you + point you back to the sheet above.
To grab a spot, simply reply to this email (these come straight to my inbox) or feel free to go straight to my calendar link + book a time that works for you.
You all get first dibs on this before it goes public next week. If you’re not sure it’s worth it, here’s a quick calculator to see how much revenue you’re leaving on the table with your current constraint(s).
Our annual plans always tell us where we need to be doing “more,” but never one for what’s leaking along the way.
I’ve even worked with a few clients where their audit came back saying their funnel is healthy + volume really is their primary constraint to growth. That answer is just as good as finding a constraint because it gives us the confidence to walk into annual planning asking for “more” with the data to back it up because that really is the answer.
Either way, run the sheet yourself or grab a spot with me to help. My only ask as you head into 2027 planning is to find out what your constraint is so you can plan around that + make a bigger impact long-term.
See you next week,
Sam
P.S. last week I dropped my new podcast, Marketing Meditations. 2 episodes are live already + ep 3 will be coming out next Tuesday (that’ll be the release day every week moving forward for new ones). Every episode, I pull one idea from a classic marketing text (Hopkins, Ogilvy, etc. - AKA the ones still worth stealing from) and translate it into something you can use in your work today.
Listen on Spotify
Listen on Apple Podcasts
Watch/listen on YouTube
Stop here before touching the levers is the most valuable instruction in the whole piece. Plenty of annual plans go straight to the spreadsheet and assume the constraint is spend, when it's often a handoff nobody owns. The warning to brief leadership before the demo line drops is wise too. A cleaner number that looks worse needs explaining before it arrives, not after.