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“A sale is made on every call you make. Either you sell the client some stock or he sells you a reason he can't. Either way a sale is made, the only question is: Who is gonna close?” - Ben Affleck in Boiler Room
The Wrong Sales Hire Costs More Than Just a Salary
The average CRO lasts less than 18 months. About 16 months, to be specific.
That stat alone should scare you; and not because sales leadership is doomed to be a revolving door, but because most companies are hiring for the wrong context.
I’ve been in the room when a CEO and the board are talking about the VP of Sales they need to hire on multiple occasions at companies of various sizes. The convo usually starts with a comment like this:
“We need someone who’s scaled a team to 100 reps before.”
That might be true.
But what if your team isn’t ready to scale?
What if you haven’t even figured out your ICP?
What if the person you just hired is amazing; just not for this stage?
I’ve realized that stage mismatch isn’t a sudden misfire. It’s a slow bleed:
Playbooks flop. What worked at $100M doesn’t work at $10M.
Pipeline thins. Reps wait for leads that don’t arrive.
Quota attainment drops. You start wondering if it’s the comp plan. (It’s not.)
Attrition spikes. Your best reps leave. New ones churn.
Board trust wavers. You start getting “helpful” intros to other sales leaders.
And the worst part? You usually don’t know it was the wrong hire until it’s too late. By then, you’ve lost two quarters, blown your forecast, and are back at square one (only now with lower morale and less board confidence).
That’s why getting the stage right matters more than getting the resume right.
The Three Stages of Sales Leadership
The following comes from a conversation I had with Paul Stansik, operating partner at Parker Gale. He’s a guru when it comes to helping portfolio companies find ‘CRO market fit.’
Not all revenue problems are created equal, and not all sales leaders are built to solve the same ones.
On the pod he laid out a simple but powerful framework: there are three core modes your company could be in, and each one demands a different type of sales leadership.
1. Figure Shit Out
You don’t really have a repeatable sales motion yet.
The founder is still the best closer.
You’re chasing signals, not executing playbooks.
You need:
A doer who can demo, close, and build from scratch.
A tinkerer with founder empathy.
A scientist who loves ambiguity and has zero fear of CRM configuration.
This is not the time to bring in someone who wants to “lead from the dashboard.”
2. Fix It Up
You’ve got motion, but it’s not working.
CRM is a mess. Win rates are shaky. No one trusts the forecast.
You need:
A triage expert who can spot where deals are stalling.
A coach who can rebuild habits without breaking the culture.
A veteran who’s been handed a dented GTM engine and knows how to tune it.
This is the person who walks in, squints at your funnel, and says, “Yeah, I’ve seen worse.”
3. Scale It Up
Your ICP is dialed in. Pipeline’s healthy. Budget’s approved.
You need:
A systems thinker who builds repeatability at volume.
A culture shaper who can maintain performance as headcount doubles.
A forecast nerd who lives in CAC, payback, and productivity curves.
This is when your GTM machine turns into a real business engine. Don’t blow it with a figure-it-out person trying to play operator.
How to Screen for Stage Fit in Interviews
Rule #1: If they wear a tuxedo, they prob aren’t a good fit.
Most interview processes for sales leaders reward confidence over context.
You don’t want the best talker. You want the best thinker—for your situation.
Here’s how to screen like a CFO, not a fanboy.
Ask about translation, not replication
“What parts of your last playbook would work here—and what wouldn’t?”
You’re testing if they know how to adapt—not just rinse and repeat.
If they can’t tell you what they’d leave behind from their last company, they’ll try to duct-tape a Salesforce Enterprise motion onto your Series B chaos.
Look for hands-on bias
“When’s the last time you personally closed a deal?”
“Have you ever rebuilt a CRM flow from scratch?”
Avoid the PowerPoint general. You need someone who’s touched the work—and isn’t afraid to touch it again.
Paul said it best:
“The average Disney World parking lot attendant gets more training than the average enterprise sales rep.”
If your candidate doesn’t obsess over enablement, you’ll be handing reps a phone and a machete and hoping for the best.
Test their problem-solving posture
“Tell me about a weird sales issue you fixed. What didn’t work before it did?”
You want judgment. Creativity. Self-awareness. And someone who doesn’t throw Marketing under the bus by minute four.
Gauge followership
“If you joined tomorrow, who’d you want to bring with you?”
Great leaders attract loyalty. No followership? That tells you something. If they light up and rattle off 5 names, you're probably onto someone who inspires trust.
And remember: salespeople are professionally persuasive.
Afterall, They wouldn’t be interviewing with you if they couldn’t sell themselves. As a CFO, I’ve always said:
“Your weapon is words. Mine is math. I’m not going to out-charm you. But I will out-analyze you.”
PSA: Don’t Promote Your Best Rep. Please.
It’s the classic move: Rep crushes quota → gets promoted → struggles in silence.
Why? Because selling and managing are totally different jobs.
Great reps:
Win deals.
Compete individually.
Thrive on control.
Great managers:
Coach others.
Analyze patterns.
Deal with humans at their worst.
When you promote your top rep, you often lose your best seller and get a mediocre manager. It’s a double hit.
Do this instead:
Create dual paths for ICs and managers.
Let reps shadow or mentor before giving them a team.
Be honest about the job—management isn’t a promotion, it’s a change of profession.
And here’s the dirty secret that few outside finance realize: At most high-growth SaaS companies, the highest-paid employee at year-end isn’t the VP of Sales.
It’s the rep who bagged five $1M deals.
“We had a rep—let’s call him Bob—who did so well that the BDRs literally built a statue to him out of empty Zyn cans. That’s your culture working for you.”
Let Bob be Bob. Because you need Bob to do Bob things to hit your company goals.
Sales Leadership Is a Stage-Dependent Hire
There’s no universal CRO.
No plug-and-play VP.
No one who can “just scale it” if you haven’t figured out what “it” is (don’t put that bad juju on them).
Sales leadership is contextual. What you need today may be wildly different than what you needed last year (or what you’ll need next).
So slow down.
Define your stage.
Interview with precision.
Trust the math, not just the charisma.
And for the love of pipeline, stop promoting your best rep unless they ask for it.
Run the Numbers Podcast
Ever heard of the Forbes 30 under 30?
What about the Cloud 100 List?
The Midas List?
I spoke to the man behind all of them. Alex Konrad is a business media legend. I spoke to him on the Run the Numbers podcast about his own company, Upstarts, a newsletter covering startups, venture capital, and the people shaping the innovation economy.
This episode covers:
Insider stories from his decade at Forbes
How lists like the “30 Under 30” were created
What it was like profiling (and sometimes singing karaoke with) the likes of Marc Benioff, Satya Nadella, and Sam Altman
The business of fund-raising announcements
How startups can actually work with journalists to shape perception
The rise of VC firms as media powerhouses
The shifting role of platforms like Substack and LinkedIn
Why relationship-driven content will outlast the race to break news
The death of traditional SEO.
Looking for Leverage Newsletter
Which company would you rather own in 5 years?
Do PE Companies Trade Innovation for Margins?
In this issue we explore all the ways to become a Rule of 50 company, and what each archetype says about your business.
PE firms often tout their operational improvements and efficiency gains. But what if these improvements are temporary and come primarily from cutting the "fat" of innovation rather than true operational excellence?
The companies that look most "efficient" on paper might just be the ones that have stopped investing in their future.
Their efficiency is a fleeting point in time.
And in a world where competitive moats are getting narrower and the cost of software production is heading towards zero, that's a dangerous game to play.
Wishing you a CRO who makes it more than two years,
CJ
