A VP of Marketing with four companies in six years crosses your desk. Immediate reaction: pass.
A RevOps leader with three roles in four years applies. Your first thought: "Can't commit."
A founding AE with three stints at seed-stage startups. Hard no you need "stability."
Meanwhile, you're building an 18-person company with eight months of runway, a product that pivots every quarter, and a GTM strategy you're inventing as you go.
Here's the contradiction: You're screening for stability you can't offer, and rejecting the exact experience you may just need.
After placing over 700 GTM professionals at early-stage B2B companies, we've watched this pattern kill more searches than any other blind spot. Founders say they want fearless, build-from-scratch operators. Then they screen for people whose resumes look like they've never actually had to be fearless.
Why This Matters Right Now
The talent market has shifted again. Seed and Series A funding is back. Capital is flowing. Top founding AEs are juggling six to eight offers at any given time. VP and CRO candidates have at least three opportunities in active rotation.
Everyone is claiming to have a rocket ship. Everyone is selling the same dream: equity upside, category creation, ground-floor opportunity.
Candidates know this. They've heard it before. Some of them have lived it and watched it fall apart.
The ones who've survived multiple early-stage companies? They've developed pattern recognition the hard way. They know what "12-month runway" actually means when burn is accelerating. They know the difference between "we're enterprise-ready" as reality versus aspiration. They know which founder promises to believe and which ones to verify.
You're not just competing for talent. You're competing for talent that's been burned before and is choosing to stay in the game anyway.
What "Job Hopping" Actually Shows You
In our post-search debriefs, clients consistently tell us they wish we had "pushed them sooner and called out their BS earlier" when they rejected candidates for tenure concerns. By the time they realized their mistake, those candidates had already accepted other offers.
We've seen VP Sales searches stretch past 150 days because founders expected the hire to "wave a wand" without understanding why their current AEs were struggling. They wanted someone with perfect tenure from a competitor instead of someone who had actually built pipeline from scratch multiple times.
The reality: The candidates who've been burned before know what questions to ask. If your answers aren't better than the last three founders who sold them a dream, you lose.
Job Hopping vs. Surviving Start Up Reality
David Matalon, founder of Venn, recently shared a story that captured this perfectly. He interviewed a candidate with five jobs in five years. His first reaction was skepticism.
But instead of moving on, he asked her to walk through each transition. What he found:
- Seed-stage startup ran out of funding in 11 months
- Got recruited to a company that realized the hire was premature
- Company got acquired, role eliminated
- PE buyout, new CEO cleaned house
- Early-stage startup lost funding after nine months
His conclusion: "This isn't a job hopper. This is someone who builds from scratch. Someone who takes risks on early-stage companies. Someone who's seen what doesn't work, and learned from it."
He moved her forward in the process.
This resonates because it's true. The "red flags" we've been trained to see are often just the reality of early-stage work. The question isn't whether someone has short stints. It's why—and what they built despite them.
The Three-Question Framework
When you see short tenures on a GTM resume, here's what to ask:
1. Did they leave or were they left?
The context that matters:
- Funding dried up, runway collapsed
- Acquisition eliminated the role or team
- Layoffs hit GTM first (it usually does)
- New leadership brought their own people
- Founder or exec team imploded
None of these are character flaws. They're startup realities.
If someone stayed at a dying company for three years, that might be the worse signal. It means they either couldn't see the warning signs or couldn't get hired elsewhere.
What good answers sound like:
"We missed our Series A target by 40%. The board gave us six months to get to profitability or shut down. GTM was 60% of the expense base. I saw it coming and started looking."
What bad answers sound like:
"It wasn't the right fit." (No specifics, no ownership, no learning)
2. What did they build or learn?
This is where you separate survivors from passengers.
For sales roles: Did they create a repeatable discovery framework? Close enterprise deals with an incomplete product? Build pipeline in three different markets?
For marketing: Did they establish a positioning framework that outlasted them? Figure out a channel strategy in a noisy category? Build a content engine from zero?
For RevOps: Did they implement systems that scaled beyond their tenure? Create forecasting models that actually worked? Build cross-functional processes?
Or did they just show up, execute the existing playbook, and wait for the beta customers to dry up?
What good answers sound like:
"I was the first marketing hire. Built the positioning framework that took us from 'another AI tool' to 'the only AI solution for compliance teams.' When the product pivoted to serve a different buyer, I rebuilt it from scratch. That taught me how to separate product features from buyer pain points in a way that survives product changes."
What bad answers sound like:
"I hit my goals." (Okay, but did you build anything that outlasted you? What did you create that the next person could use?)
3. Are they still in the game?
This one matters most.
After getting burned two or three times, are they still willing to bet on early-stage? Are they still taking calls from seed and Series A companies, or are they only looking at Series C and later-stage now?
If they're still here, still interviewing at 15-person startups after watching two others implode, that's not naivety. That's belief. You cannot teach that.
What good answers sound like:
"I could take a senior role at [established company] tomorrow. But I've learned I'm better when I'm building from scratch. I know what questions to ask founders now. I know what good runway looks like versus fake runway. And I know I do my best work when nothing is figured out yet."
What bad answers sound like:
"I need a job and you're hiring." (Fair, but where's the conviction? Where's the learning?)
The Pattern No One Talks About
Candidates who've only worked at one successful GTM organization often can't tell you why it worked.
They know the playbook. They can execute it. But they don't know how to write one.
They've never had to build pipeline in three different markets with three different ICPs. They've never had to reposition a product mid-quarter because the original messaging wasn't landing. They've never had to close deals when the product roadmap is vaporware and the only proof points are screenshots.
The ones who survived a few failures? They have scar tissue. They know which shortcuts work and which corners you can't cut. They've seen funding fall through, pivots happen mid-flight, and strategies change underneath active campaigns. They kept going anyway.
That's the profile you actually need. You just have to ask the right questions to find it.
Why We Keep Getting This Wrong
The lazy pattern-matching problem:
Everyone is looking for the same profile. "Give me someone from [successful competitor] who's already proven at a unicorn."
What you're really saying: "I want someone another company de-risked for me."
You're overindexing on signals that highlight where OTHER companies took a chance on a candidate, then refusing to take that same chance yourself.
The unicorn fallacy:
People aren't born at successful companies. Every high-performing GTM leader at a well-known company had a first startup job where they took a risk on an unknown brand, an unproven product, and an uncertain outcome.
Someone gave them a shot before they had the pedigree.
Now you expect candidates to appear with that pedigree already built—without acknowledging that building it requires taking risks that might not pan out.
The spirit contradiction:
Think about who actually says yes to a 20-person startup:
Someone willing to take calculated risks. Someone comfortable with ambiguity. Someone who can build without a roadmap. Someone who "speaks founder" because they've been in the trenches.
Then we reject them because their resume shows they've... taken calculated risks at early-stage companies.
We're punishing the exact spirit we're recruiting for.
What To Do Differently
Before you screen anyone out for tenure:
Look for patterns, not just dates. Are all the departures clustered around 2022-2023? That's not a character issue, that's the market downturn. Are the companies all seed or Series A? That's not job-hopping, that's specializing in early-stage.
During the interview:
Make them walk through every transition. You'll know within ten minutes whether they learned anything or just got repeatedly unlucky. The best candidates will have specific, tactical learnings from each experience. The weak ones will have vague answers about "culture fit."
In your debrief:
Ask yourself: "Am I rejecting this person because they took risks I'm now asking them to take again?" If yes, you're screening for the wrong thing.
When you make your case to leadership or board:
Frame it correctly. It's not "this candidate has three short stints." It's "this candidate has built GTM from scratch three times, in three different markets, with three different products. They know what breaks and how to fix it before it becomes a crisis."
The Hard Truth
You can't ask candidates to be fearless and then only hire people who've played it safe.
You can't demand build-from-scratch mentality and then reject anyone who's actually built from scratch at companies that didn't make it.
You can't sell candidates on equity upside and category creation, then blame them when the previous founder's rocket ship ran out of fuel.
Either you want the calculated risk-taker who knows what early-stage chaos looks like, or you want the pedigreed hire from a stable company who's never had to figure it out without a playbook.
But you can't have both.
And if you're only comfortable hiring someone after a Series C company has validated them for you, you're not really building an early-stage GTM culture.
You're just late.
