Yesterday was my last day at Loxo

Real talk: how I knew it was time + decided what was next

Yesterday was my last day at Loxo.

Feels weird to write that out after spending the last 3.5+ years there. In some ways, it feels like just yesterday that I joined the team to build out the marketing program. In other ways, it feels like 35+ years there with all that the team experienced + accomplished during that time.

Early in my career (and to this day, TBH), I’ve always been curious about why people move on from companies. Were they actively looking? Was something going on behind the scenes? What factors did they weigh in deciding what to do? How + why did they ultimately make the decision?

So thinking about this + recognizing that these essays are ultimately for myself to “write” out loud + to come back to months/years later, now seems a pretty good time to reflect on those same questions for myself. And hopefully in going through this, it’s helpful to some of you reading this, now or in the future. Whether it’s to be used as sound advice or a cautionary tale in what not to do, that’s for you to decide :)

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Sponsor: Affect

Affect is the framework for how I think about marketing accountability. The playbooks I’ve built from 15 years of seeing what works + what doesn’t and recognizing that the purpose of marketing isn’t to hit vanity metrics like MQLs, but to move the business.

Affect is for the marketers who have sat in a room where marketing celebrated surpassing its MQL targets while the business missed revenue. It’s for the marketers who want to be held accountable because they’re confident enough in their work to let the math speak for itself. It’s 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.

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Why now?

I was going to start this off with some notes of appreciation, but putting myself in the shoes of anyone reading this + myself when I see/hear of others moving on, I figured we’d start off by addressing the elephant in the room:

Why are you leaving? And what led to that decision?

The simple answer: it was time.

To be clear, I'm not walking into the unknown here - I know what's next + everything’s lined up at this point. But one thing I’ve noticed over my career is that there’s this little thought/feeling that slowly starts to creep in daily at work. That something’s missing, or that I’m “slowing” down in terms of what I’m learning + executing.

There’s a Steve Jobs quote from a commencement address he gave at Stanford where he said "For the past 33 years, I have looked in the mirror every morning and asked myself: 'If today were the last day of my life, would I want to do what I am about to do today?' And whenever the answer has been no for too many days in a row, I know I need to change something."

That quote is about the closest thing I can point to that describes what this felt like. It wasn’t one specific thing/issue that set it off, just a slow accumulation of mornings where the honest answer to that question was no.

I also want to be clear on one thing - this was entirely my call. Nobody pushed me out + nothing went off the rails internally. We just had our biggest product rollout in history + are continuing to grow. This decision was me choosing to move on to what’s next.

The slightly longer answer: months’ worth of reflection, questions, discussions, and the longest pros/cons list I’ve ever made.

To keep using the Steve Jobs quote, I’d been reflecting on the “mirror test” for a number of months. A career decision shouldn’t ever be made in a rush or in a “peak” season of any specific emotion. Nor is it ever a binary decision where 1 criteria decides if I should stay/leave. So every day, I’d be running through countless questions + thoughts in my head like:

Do I stay + hope things get better on their own? Just wait it out?
Do I stay, but proactively try to make things better myself?
Do I say enough is enough + leave without a plan, trying to figure it out after?
Do I stay until I have a plan, no matter how long that takes, despite the answer to the Steve Jobs mirror question being “no”?

Each of those questions carries a different type of weight. Risk, patience, trust, happiness, etc., and every week, the values/answers for each would change.

So me being me, I did what I always do when I don’t have a good answer for something or there are too many unknowns to make a decision - I created a framework to help me work through it.

One thing I’ve learned about myself is that I genuinely love + enjoy the “0-10” work (note: when I say 0, 10, 100, etc. in here, I don’t literally mean $10M, $100M, etc., using this more metaphorically). Getting a lay of the land, understanding the goals/outcomes we’re after, and putting a plan in place to work toward it. Then, and most importantly, doing the actual work to drive said outcomes.

I’ve always been very hands on in what I do. Living in just the strategy world sounds good in theory, but is very boring in practice AND since you aren’t executing anything, you never truly learn + understand if the strategy works. Nor can you iterate on things via the “fingertip feel” you can only develop via years of experience, failures, + first principles.

As things start to near the “10” mark, that’s often when teams start to get bigger, more cooks enter the kitchen, + the maturity of the company dictates that certain things need to change (as they should). And it’s then from the “11-100” type work that I find, while I can do it, it’s just not as much fun for me.

“Sam, please tell me you’re not about to say that when work isn’t as much fun as it used to be, that becomes the tipping point for when you start thinking about what’s next…”

🤷‍♂️

That’s exactly what I’m saying.

At least at this point in my career.

Naval Ravikant put this so eloquently + concisely that I’m just going to leave this 48 second video here so you can watch/hear it for yourself (I promise it’s worth it):

TL;DR = “find what feels like play to you, but looks like work to others”

In the early days of my career, I’ve always said eating shit is simply part of the path. There will be jobs I don’t love, tasks that are far from enjoyable that need to be done, people I won’t like working with, + so on.

BUT, that doesn’t mean all of those things aren’t valuable. They’re experiences that helped me orient around what I do like to do and would use as waypoints as my career progressed to gradually put me in places + positions I did enjoy and would succeed in.

So I think this segues well into the second part of the question…

How’d I make this decision?

It’d be easy to say there’s always 1 silver bullet that makes the decision for you. That you’ll get paid more, or that the hours are better, or that it’s working with a company/leader on your “dream” list.

But even when I’ve been offered a salary that’s 2-4x your current rate, or at a company with an incredible leader, I’ve found that those still don’t make the decision for me. That the timing isn’t quite right because I haven’t learned what I need to in this role, or that the team you’re already a part of is truly special and greater than that one individual leader/company.

So in reflecting back on how I made this decision to move on to what’s next after Loxo, I thought I’d share the incredibly over-thought, over-analyzed, over-everythinged things that passed through my mind, were written down in list after list, + anything/everything on top of that.

While at first, most of us would go to drafting a list of what we do want in a future role, I’ve found it’s actually helpful to first start off with what I don’t want in a future role. And back to a few paragraphs ago, this list is often fueled by all the experiences I’d had to date + noting what I didn’t enjoy so I could make sure I avoided that in the future.

And this is what led me to my first list of “absolutely-nots” for deciding what’s next:

• No publicly-traded companies (too much short-term decisionmaking due to quarterly earnings reports)

• No VC-backed companies (similar to the above, lots of decisionmaking to grow/scale at any cost + seeing some where ethical behavior is viewed as optional)

• Not serving a market where the ICP/buyers are unprofessional (rough mental model for this is “did the individual I sell to go to school to get into their profession?”). This one might ruffle some feathers + is 100% opinion on my side after experiencing selling to those who did/didn’t do this.

• No role where the expectation was simply to be a “channel executor” vs. someone who looks at the entire growth ecosystem to understand the best way to acquire new customers. This one pairs nicely with the common adage of “don’t work for a CEO who doesn’t get marketing”

• No role where I wouldn’t be paid more than what I’m currently making (because inflation + supporting a family 🤷‍♂️)

• No huge teams. As I noted above, I like the “figuring it out” stage of things vs. “scale what’s working + don’t question what’s working because it’s what we’ve always done” environment

Only 6 items, but they whittle the list down a LOT. And in reading between the lines on all of these, that showed me what I was ultimately looking for were:

• Ownership + autonomy. Ownership meaning having some type of stake in the company + the results. Autonomy branching off of that meaning having the trust + authority to make decisions that I believe would drive the type of results that would benefit me as someone with an ownership stake.

• An environment where the “old way” is recognized as no longer effective + that improving upon this is not just what’s needed, but actively looked for to be solved by the role (and ideally, this is for both the market being served and the company’s view on marketing/GTM)

These two “lists” quickly gave me shortlists for what I thought would be the best environments for me to be in next. So once I worked through them + sifted various companies through them, I was able to then run them through the final grinder to help me see which opportunities truly were great, which were ok, and which ones may have sounded good (aka great pay), but when including all of the other factors, I could quickly see that that one benefit was far outweighed by other factors that I knew I wouldn’t enjoy.

So with that all in mind, here’s what “the grinder” looked like using the various criteria I wanted factored in to helping me make this decision:

Must haves

• Remote-based work (no mandatory days in office/relocation required)

• Total comp ≥ current comp

• Company has already established product/market fit

• No “90-day pipeline/revenue miracle” expected

• ≤ 1 layoff in the company’s history

• Love the actual day-to-day work itself

• Professional ICP

Strong preferences

• Direct leader is someone I respect

• Real autonomy in the role

• Internal transparency (decisionmaking, financials, etc.)

• Leadership trusts my strategy/philosophy

• Marketing is respected within the organization

• Strong category tailwinds

• Founding team created the company from their own conviction in the product/service (not simply seeing where the most market $$ is available)

• Customers truly love the product/service + actively praise it to peers

• Product/service I have enthusiasm about/happily geek out learning

• Upward comp trajectory

• Some type of equity (ownership, shares, etc.)

• High quality team (skills AND as human beings)

• Long-term founder commitment (not looking to cash out ASAP)

Nice to haves (I had 20+ here, so just sharing a few as examples)

• Personal brand compatibility (day-to-day fuels what I learn + share via these newsletters, on LinkedIn, etc.)

• Continuous learning opportunity

• Internal culture of heavy peer collaboration/knowledge sharing

• Sell to a single ICP (not multiple)

• Company has a strong reputation in the market

The hardest part

This is the part I skipped above. The “shoutout to my incredible team” paragraph/appreciation bit is what’s expected because it’s the politically correct thing to do. List off the company leadership, how much you grew during your time, yadda yadda…basically something safe + forgettable.

The honest to god hard part for me are the team members I won’t get to talk to every day. One thing that was unique + special for me in this role is that in growing the team from myself as a solo-marketer to a team of 10, I recruited/hired every single member. No one was “inherited” or mandated as part of my team, so in being the final decisionmaker for hiring here, they were all people I knew I would want on the team + enjoy working with every day.

And call me crazy, but I actually care about my team. An easy 25-50% of our weekly 1:1s were NOT about work. I wanted to learn what they cared about outside of the 9-5 here - what their hobbies were, hearing the fun family dynamics most have with spouses and/or kids, what personal goals they had set for the year, etc.

One team member is currently on a trip in Italy + we already have a call scheduled when they’re back so I can hear all about it. Another team member is due to have their first child within a few weeks + most all of our conversations over the past month have been about that (and Chick-fil-A’s newest menu releases - IYKYK). Another member of the team actively tries to work themselves to the bone, so we had a bet going where if they didn’t get an agreed upon number of hours of sleep per night, they’d send me $20.

These are the conversations + dynamics I’m going to miss. They’re real relationships + like a friend who moves out of town, just because the proximity may have changed, the actual decision to continue/end the relationships with each person is simply a matter of effort + maintaining them after the “work” 1:1s are no longer scheduled.

So why am I sharing this section? As you can tell, it’s not for them as I’m not sharing any names here. I’m sharing it because the team was what kept me in the role far longer than I would have had those incredible relationships not been in place. This is always the hardest part of voluntarily leaving any company + is one I’ll always say not to underestimate. I know I shared the whole “list” above for how I looked at each potential company, but one thing that is missing from that is the “stay” column for Loxo + the weight that the single row of “team” carried was far greater than any + all of the other rows combined.

What’s next?

A week of digital detox.

Going to stash the laptop in a cabinet + spend lots of time with family, putting a dent in a stack of books I’ve been wanting to read, + some good old fashioned manual labor/work around the house. It may be weird, but as someone who lives in a very digital world, there’s something cathartic to seeing an improvement between the before/after of something tangible.

That said, no newsletter next weekend + stay tuned the following week as I’ll share where all of the above thinking + analyzing led me to 🤗

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See you next week,
Sam

P.S. know a marketer who’d enjoy these newsletters as well? Reply back to this email (so I get it) + cc them on it. As a small thank you, I’d be happy to help answer any questions you have or hop on a call sometime for a fun marketing session :)