I’ve seen it again and again across 30+ investments, 10+ unicorns, and hundreds of portfolio company board meetings.
There’s one pattern that predicts VP failure better than anything else I’ve seen. Not their resume. Not their pedigree. Not even their interview performance.
It’s whether they still do the actual work themselves.
Let me break this down by function, because the pattern holds true across every C-level and VP role:
CROs Who Don’t Sell
Every time I see a CRO that doesn’t sell themselves, they fail.
Not “occasionally jump on calls.” Not “review deals at the end.” I mean actually carrying quota. Actually running discovery calls. Actually negotiating contracts. Actually closing deals.
The best CROs I’ve worked with—the ones who took companies from $5M to $50M+ ARR—never stopped selling. They’re in the CRM. They’re on calls with enterprise prospects. They’re working the biggest deals in the pipeline.
Why? Because the moment you stop selling, you lose:
- Feel for what’s actually working in the market right now
- Credibility with your team (they know when you can’t do what you’re asking them to do)
- Ability to coach effectively (you’re coaching from theory, not practice)
- Understanding of where the real bottlenecks are in your process
I’ve watched CROs who were “too senior” to carry a bag struggle to diagnose why conversion rates were dropping. Meanwhile, their quota-carrying counterparts could tell you exactly which objection was killing deals because they heard it three times that week.
CTOs Who Don’t Code
Every time I see a CTO that doesn’t code themselves, they fail.
And I don’t mean writing trivial scripts or reviewing PRs from a distance. I mean actually shipping features. Actually debugging production issues. Actually understanding the codebase deeply enough to make real architectural decisions.
The best CTOs I know are still in the code multiple times per week. Not because they don’t trust their team. Not because they’re control freaks. But because:
- You can’t make good technical decisions without understanding implementation reality
- Your technical team immediately knows if you’ve lost your edge
- The complexity gap between what you think the product does and what it actually does grows exponentially when you’re not in the code
- You miss the small friction points that slow down your entire engineering organization
I’ve seen this play out dramatically. CTOs who code know exactly why a feature took 3 weeks instead of 3 days. CTOs who don’t code just see “engineering is slow” and can’t fix it.
With AI/Cursor/vibe coding, this matters even more now. The modern CTO should be 10x more productive in the code than ever before. If you’re not using these tools to stay technical, you’re falling behind.
CMOs Who Don’t Generate Pipeline
Every time I see a CMO that doesn’t market themselves, they fail. Specifically, that don’t generate pipeline themselves.
This one surprises people, but it’s just as true. The best CMOs I’ve worked with are writing content. Running experiments. Building campaigns. Getting their hands dirty with the actual tools and tactics.
Bad CMOs delegate everything and become “strategy people.” They have opinions about brand positioning but haven’t written a piece of content in 18 months. They have thoughts on demand gen but haven’t built a campaign themselves in years.
Great CMOs are:
- Writing thought leadership pieces themselves (not just editing what their team writes)
- Testing new channels and tactics personally
- Understanding what’s working in the market because they’re in the tools daily
- Building content that actually generates pipeline because they know the customer
You can’t be a great CMO from 30,000 feet. The best marketing is too nuanced, too tactical, too dependent on understanding what actually resonates right now.
CCOs Who Aren’t Meeting Customers
Every time I see a CCO that isn’t constantly meeting with customers themselves, in person, they fail.
This might be the most important one. Customer success is won and lost in the details of customer conversations. The CCOs who win are the ones who:
- Are on planes visiting customers constantly
- Know the top 20 customers by name and recent history
- Can tell you exactly what the biggest customer pain points are right now
- Have credibility with the team because they’re doing the hardest customer saves themselves
I’ve watched this play out in painful ways. CCO brings in “process” and “systems” but stops meeting with customers. Churn starts creeping up. By the time they notice it in the dashboard, it’s too late. The best CCO would have seen it six weeks earlier because they were in customer meetings and heard the early warning signs.
Customer success is not a reporting exercise. It’s a relationship exercise. And relationships require presence.
Why This Matters More at Scale
Here’s the thing people get wrong: this doesn’t just matter at the early stage. It matters more as you scale.
I know many will disagree. The conventional wisdom is that executives should “work on the business, not in the business.” That past $10M or $50M or $100M ARR, executives should be pure strategists and managers.
That’s wrong.
Maybe this works at a huge public company where you have 10 layers of management and the executive team is purely allocating capital and setting strategy. But not before $250M ARR. And probably not before $1B ARR. If ever.
The Scaling Paradox
Here’s what actually happens as you scale:
The details matter more, not less. At $50M ARR, a 2-point decrease in win rate costs you $1M+ per year. At $100M ARR, it costs you $2M+. You can’t afford to be disconnected from what’s actually happening in deals, in code, in campaigns, in customer conversations.
The best executives get leverage from doing, not from delegating. When your CRO closes a $500K deal, they don’t just generate revenue. They:
- Create a case study the whole team can learn from
- Establish patterns that become repeatable process
- Build credibility that makes their coaching 10x more effective
- Spot market shifts before they show up in the data
Manager-only executives become bottlenecks. If you can’t do the work yourself, you can’t:
- Evaluate whether someone is actually good or just convincing
- Make fast decisions because you need to wait for analysis
- Spot problems early because you only see lagging indicators
- Coach effectively because you’re teaching theory instead of practice
The Real Issue: Pretending Otherwise
The real issue I see is when founders sort of know this, but make the VP / CXO hire anyway. They like how they talk, where they work, and whom they seem to know. Great. But will they be hands on keyboard? Will they really do the work?
Test it.
The AI Era Makes This Even More Important
With AI tools like Cursor, Claude, and ChatGPT, the productivity gap between doers and non-doers is growing exponentially.
A CTO who codes with Cursor is 5-10x more productive than they were two years ago. A CTO who doesn’t code has fallen further behind because their team’s productivity jumped but their understanding didn’t.
A CMO who writes with AI can produce more high-quality content than an entire team could before. A CMO who doesn’t write can’t evaluate what good looks like anymore.
The tools have changed the game. Executives who stay hands-on have superpowers. Executives who don’t are becoming obsolete faster than ever.
What This Means for Hiring
When I’m helping portfolio companies hire VPs and C-level executives, I always look for this:
In interviews:
- Ask them to do the actual work. Have CRO candidates run a discovery call. Have CTO candidates review code or design architecture. Have CMO candidates critique and improve your messaging.
- Ask detailed questions about their craft. If they can’t go deep, they’ve lost it.
- Look for recent examples of them doing the work, not just managing it.
In references:
- Ask “Do they still do the work themselves? When was the last time you saw them close a deal / ship code / create content / meet with customers?”
- If the answer is more than a month ago, dig deeper.
In the first 90 days:
- Watch whether they jump into doing the work or just set up meetings and build process.
- The great ones will carry a bag, ship code, write content, visit customers.
- The bad ones will hide behind “strategy” and “building the team.”
Do They Still Do The Work? If Not, Don’t Make The Hire
The #1 clear sign a VP will fail is simple: they’ve stopped doing the actual work.
It doesn’t matter if they’re a CRO, CTO, CMO, or CCO. The pattern is identical. The executives who stay close to the craft win. The executives who become pure managers and strategists lose.
This is especially true before $250M ARR. Maybe even before $1B ARR. The companies that win have executive teams that can still do the work at the highest level, even as they build and lead teams.
If you’re hiring executives and they’ve “graduated” beyond doing the actual work, run. If you’re an executive and you’ve stopped doing the work yourself, get back in the game or you’ll fail.
I’ve seen this play out too many times to ignore it.
30+ investments. 10+ unicorns. The pattern is crystal clear.
Stay hands-on or fail. It’s that simple.
