In my last column, I offered advice on defining job descriptions around what you need, rather than picking a title out of The Book. This column is about how you describe the person you want to fill that new role.
Founders describing the person they wish they could hire almost always reach for the same word. Senior. They want someone senior in engineering, senior in sales, senior in operations. They want someone with real experience, someone who’s done this before, someone they can hand a hard problem to and trust it will get handled.
It’s a reasonable thing to want. It’s also, more often than founders realize, a person who doesn’t exist, and understanding why is the first step toward hiring someone who does.
When you say “senior” and mean 10 to 15 years of experience, you are not just describing a skill level. You are describing a person, and that person has a life. They’re probably somewhere in their late 30s to mid-40s. They likely have a family, kids who are settled in a school, a spouse with a career of their own that isn’t going to relocate on a whim. They’ve been in the workforce long enough to be thinking, at least in the back of their mind, about retirement savings, about the trajectory of the next 15 years rather than the next two.
These are not, by and large, people who are looking to take on the kind of risk that an early-stage company represents. It’s not that they lack ambition or vision. It’s that the shape of their life has settled around stability in ways that make walking away from it, for an uncertain paycheck and an equity stake that might be worth nothing, a genuinely bad trade.
It has nothing to do with how talented or curious they are, and everything to do with what else they’re responsible for. If you’re picturing that person applying to your seed-stage company, you’re picturing someone whose life circumstances may make that choice close to irrational.
So who is available to you? Setting new graduates aside (plentiful, but a separate conversation, mostly about training overhead), there are really two profiles worth understanding.
The first is what I’d call intermediate: someone with five to seven years in the workforce. They know a job. They’ve built real competence. And they’ve usually started to notice something uncomfortable about where they are. There is a stack of more senior people above them who aren’t leaving anytime soon, and a growing sense that their own progress is going to be slower than they’d like inside that structure.
They may be married. They may have young children. But they haven’t fully settled into the kind of life that makes risk unthinkable. It is not uncommon for someone in this position to genuinely be looking for two things that you can offer: a new challenge, and the chance to be part of building something rather than maintaining it.
If you offer this person real equity, not a token gesture, you will be speaking directly to where they already are in their own thinking. They’re not taking a leap of faith so much as taking an opportunity they were already looking for.
The second profile is close to the opposite end of a career, and I’ll admit this one is a little self-referential. This is someone who has already been successful, who has built or run something, and who is tired of carrying the weight of being responsible for outcomes. They don’t want to be the one accountable anymore. What they do want is to stay involved in things that matter, at a pace and a stress level that don’t consume them.
Compensation is rarely their primary concern, because they’ve reached a point of financial security where that’s no longer the driving question. What they’re looking for is meaning without the burden of accountability. This is a person you might be able to bring in part time or on contract — and one of the best uses of that arrangement is having them mentor the first kind of person you’ve hired, rather than putting them back in charge of anything. If they are like me, they’re done being in charge. They’re happy to help someone else get good at it.
Put those two together and something interesting happens. You’re not settling for a lesser substitute because the mythical senior hire wasn’t available. You may actually be assembling more of what you needed. You are getting ambition and energy on the one hand, and hard-won judgment on the other, instead of a single 15-year veteran who arrives with their own fixed way of doing things and a lot of other responsibilities outside of work.
This really gets at the deeper problem with the word “senior” itself. When founders use it, what they actually mean is someone experienced and competent enough that they can hand over something that matters and trust it will get done, someone they can come to rely on quickly, without a long runway of watching and correcting. That’s a completely reasonable thing to want.
The mistake is assuming that years of experience is what delivers it. Sometimes it does. But founders also need to get comfortable with something that takes a bit of getting used to: the whole point of hiring someone who isn’t you is that they’re going to do things differently than you would. That’s not a bug; it’s the plan.
A person who arrives with 15 years of strongly held opinions about how the job should be done is sometimes a worse match for that goal than someone with less mileage and more openness. Understand that what you’re looking for is new ways of thinking, not just a different pair of hands doing it your way. But you need someone who will adapt to your culture and your circumstances: someone who thinks differently but wants to build something new, not recreate their own comfortable reality.
“Senior” is really jargon. It’s a standard label. And because of that everyone knows what it means. And everyone has a different definition. It tells candidates one thing about themselves and tells founders something else entirely about what they hope to get, and the two don’t always describe the same person.
Which brings me to the thing I think matters most when you meet candidates for any position, and it’s the question I’d put ahead of every other qualification on the page.
Do you want to work with this person? Would you genuinely enjoy seeing them every day?
And just as important, are you going to build a job and an environment that they will be motivated to show up for?
Everything else is, in a real sense, secondary. I’ve watched this play out often enough now to say it plainly: if you find people you like working with, who want to work with you, you will find a way to turn them into productive employees over time. Skills develop. Judgment sharpens.
Fit and mutual motivation are the raw material that competence gets built on. But if you hire someone you have quiet reservations about, or who isn’t actually motivated by the way you and your company work, none of their qualifications will save the relationship. It doesn’t matter how experienced they are, how impressive their résumé looks, or how strong the interview was on paper. Eventually, and usually sooner than anyone would like, you’ll part company.
The title was never the thing that mattered. Nor were the years. What mattered was whether the two of you wanted to be in the room together, building something you would both be proud of.
Hire for that.