The Peter Principle is real, and in high-growth tech it hits fast and hard. The brilliant engineer who built your first product gets promoted to VP Engineering. The scrappy PM who shipped your MVP becomes Head of Product. They earned it — their work got you here. But “got you here” and “will get you there” are two very different things.
We went through this at Rippling. After years of triple-digit growth and hiring thousands of people a year, we hit a point where we needed to uplevel — to bring in senior leaders who could take the organization to its next level and manage the same high performers who had built the foundation of the business. It’s one of the most consequential decisions a scaling company makes, and most get it wrong. What follows is the framework we’ve built for getting it right: how to know whether you need a builder or an operator, and how to actually test for it before the offer goes out.
Define what you’re actually looking for
The Peter Principle in practice means a strong individual contributor (IC) who kept getting promoted — exceptional at the work, then rewarded with people, then more people, until they were running an organization they were never trained to lead. That’s a builder in the wrong seat.
The natural response is to go outside. To hire a real operator — someone with genuine leadership experience who has managed through hard moments, built teams, and scaled functions before. They don’t need to reinvent the wheel. They just need to make it run better.
But that’s exactly where the second mistake happens. Companies go looking for an operator and end up hiring someone who is neither. A leader who has climbed too high and lost touch with the actual work. Someone with an impressive title but no instinct for the grind — who hasn’t been close to the product, the customer, or the details in years.
The pedigree trap
The easiest hire is the obvious one: strong school, big tech pedigree, climbed the right ladder. On paper, they’re perfect. But can they run as hard as you need them to? When was the last time they actually looked at code, reviewed POs, or talked directly to a customer? Have they been living in spreadsheets for the last three years?
Pedigree tells you where someone has been. It doesn’t tell you whether they’ll swim or sink in your environment.
Two things we screen for before anything else
Before we get to interviews, there are two filters that have proven invaluable.
Have they seen great? Specifically — have they been part of an A team? There’s something that happens to people who’ve experienced what a truly high-performing team feels like. They don’t want to be part of anything else. They carry higher standards and know the difference between good and exceptional. We look for that.
This matters even more at the executive level. An IC who hasn’t seen great underperforms, but still has a chance to learn. An executive who hasn’t seen great sets the bar for an entire team — and that bar will likely be low.
A note on what this isn’t: “seen great” isn’t about brand names or prestige. It’s not about whether someone worked at Google or went to Stanford. It’s about whether they’ve been in a room where the bar was genuinely high, where they didn’t settle for ‘good enough,’ and whether that experience shaped how they operate.
Are they someone who’ll stick around? Past tenure is a signal — not because short stints are automatically disqualifying, but because executive leadership is tested most in hard moments. Organizations go through product failures, leadership changes, market shifts. You need leaders who know how to rally their team and push through, not exit at the first sign of turbulence. Layoffs happen, companies fold, situations change — one departure rarely tells you much. But if someone has never stayed through a hard moment at any company in their career, that’s a pattern worth probing directly. The explanation they give matters as much as the history.
The interview process: assessing the fit
This is where most companies get it wrong. They interview executives like executives — high-level conversations about vision, strategy, leadership philosophy. Then they’re surprised when the hire can’t operate.
Over 30 VP-level candidates have made it to our final round and failed. Not because they weren’t talented — many were. But they weren’t hands-on anymore. They’d been managing managers long enough that they’d lost the muscle for getting into the weeds. In a high-growth environment where the infrastructure isn’t built yet, that’s a fatal gap.
Our process is designed to expose exactly that gap. We put our VP-level candidates through the same interview assessment as ICs: a case study built around a real problem they’d be expected to solve daily — and likely debate directly with the CEO and customers.
The interview is done live, with a panel of three. We expect candidates to come in having done deep research and to present a working prototype: walking us through the user experience journey, the decisions they made, the edge cases they considered, and the trade-offs they weighed.
We ask hard questions, and we don’t excuse weak answers by attributing them to rustiness or being “too senior to be hands-on.” Bad product judgment doesn’t change over time, nor does it get better.
The second thing we’re evaluating is how quickly they think on their feet. Getting every idea right isn’t the standard — what matters is whether they can adapt when challenged, change their mind when the evidence warrants it, and stay in a productive conversation under pressure. It doesn’t matter whether that pressure is coming from a peer, a cross-functional partner, or the CEO. The questions that reveal this aren’t about what the candidate has done. They’re about how they’d approach a specific problem today, with the resources you actually have — not the resources they had at their last company.
My background is in technical recruiting, but I’ve seen this play out the same way across every function. The format adapts — a sales leader might do a live pipeline review instead of a product prototype — but the principle is the same: show me your work, not your vision.
Reference checks
Your candidate has cleared the interview. In our experience, only 20% of candidates make it this far. You’re excited — but you need more signal before you commit.
We ask for five references. A lot of people treat this as a checkbox: “candidates only give names of people who’ll say good things anyway.” That’s true. It’s also your job to make the most of every conversation.
Start with the reference themselves. Were you impressed by them? Would you want to hire this person — or work for them? Do they seem to know the candidate deeply, or are they just vouching? The quality of a reference tells you something about the quality of the relationship — and about the candidate. Someone who has built strong, lasting relationships tends to have references who can speak to them with real depth and specificity. A surface-level reference that doesn’t give you much is a signal on its own.
On content: ask deep questions. “Tell me more about them” won’t get you far. Try these instead: What should someone considering hiring them know about them? How have they changed over the time you worked together? What would their harshest critic say? And finally — if you were to stack-rank them against others you’ve seen in similar roles, where do they land and why?
When you ask that last question, listen carefully. If you hear “top 25%,” that’s not what you want. You want “top 2–5%.” Anything short of that, dig in — and hold it against what you know this role requires. Do they still look as strong as they did on paper?
The anti-sell
Before you extend an offer, do one more thing: level with the candidate on what working here is like. Give them the worst of it.
A wrong VP hire costs you six months of uncertainty plus time in damage control. The anti-sell isn’t pessimism — it’s a forcing function. The right candidate hears about the pace, the ambiguity, and the things that aren’t built yet, and leans in. The wrong candidate starts to hedge. You want to know which one you have before the offer goes out.
What good looks like
When you get this right — when you find someone with the right background, the longevity, the hands-on instincts, and the appetite for your specific stage of chaos — something clicks. They don’t just fill the role. They raise the ceiling for your team.
The executives who’ve worked out for us were the ones who passed every filter above — including the ones who nearly talked themselves out of the role during the anti-sell, then called back a week later to say they were in.
The six months you lose to a wrong executive hire isn’t just time. It’s the momentum of a team that was waiting for someone to show them what great looks like. The framework above won’t guarantee a perfect hire. But it will tell you, before the offer goes out, whether you have the right type of candidate in front of you.
