It can make a ton of sense to take risk when it comes time to hire your VPs and C-level execs. Risk they don’t have industry experience. Risk they only have experience at one stage earlier. Risk on a stretch candidate.
But please trust me there is one risk you just cannot take. Especially before $100M+ ARR, and really maybe before much, much later.
You cannot hire executives who won’t actually do the job themselves. Trust me. They always fail. It’s too competitive, there is too much to know even in late stage start-ups. It’s not all managing managers. Maybe it is at Salesforce or Oracle or MongoDB. It is not even at $150M ARR.
Your executives MUST do the job themselves, too. At least, partially.
The CRO Who Has No Deals of Their Own
You can spot this one easily in the first board meeting. And in all the interviews, if you really ask. The CRO presents the forecast, the general pipeline coverage, the hiring plan, the comp plan. Ask about a specific deal and the answer is “let me check with the exec on that.”
The CROs who work are:
- in deals, at least the important ones
- They take calls with the biggest prospects
- They fly out to close
- They know the champion’s name and the procurement lead’s name, and they have a handful of accounts where the buyer texts them directly. They still run the forecast, and they know which parts of it are real because they were in the room.
Marc Benioff still meets with 100s of customers in person each year. Did your new CRO do the same their first week? So many really just want to … manage. And run the process from their last company.
The CRO who only manages gets told what the reps want them to hear. Their forecast is a roll-up of other people’s optimism. The best reps figure out fast that their boss can’t help them close anything, so they stop asking. Then they leave.
Sales slows. Win rates go down. Existing customers get pressured the most to make up for it.
The CTO Who Stopped Committing Code
The classic example: you hire a VP Engineering from Box, or Cloudflare, or whatever big B2B company. Or even just a unicorn. And they know how to manage teams, sort of. But they haven’t committed code in years.
Do Not Hire Them. Everything will slow down. Almost immediately.
This was already a problem pre-AI. In 2026 it’s fatal. The way software gets built changed completely in the last 18 months. A CTO who isn’t hands-on with AI coding tools every week can’t tell you what a team of 5 can ship now. That means they can’t size the team, can’t call out a padded estimate, and can’t tell which of their engineers have adapted.
I’m not an engineer and we ship production apps every day at SaaStr AI . If the CEO is shipping and the CTO isn’t, you have the wrong CTO.
The CTO doesn’t need to own the critical path. They need to ship something real, regularly, and review real code. They need to truly be at the cutting edge. Because you have to be, too. Don’t cut this corner because they were a VP or Director of Engineering at a Well Known But Large and Not That Fast Growing B2B company. Don’t do it. Please.
Innvoation Dies.
The CMO Who Manages a Budget and Three Agencies
Ask this CMO who owned the revenue commit. Who wrote the homepage. An agency. The launch email? The content lead. The webinar deck? Product marketing. The face of the company on LinkedIn? The CEO, by default.
The CMOs who work:
- Own the commit, and know how to hit it.
- Write. They write the positioning themselves. They rewrite the subject line an hour before the send.
- They know why last month’s campaign missed, because they built part of it.
When the leader does none of the marketing themselves, the function turns into coordination: a calendar, a budget, a dashboard of MQLs. Pipeline from marketing flattens, and the explanation every quarter is attribution.
The CMOs who don’t truly generate demand … lead to less of it, not more.
The CCO Who Reads Health Scores and Never Gets on a Plane
Do not hire a Chief Customer Office or VP of Customer Success that doesn’t go visit customers their first week. And do not hire one that cannot improve onboarding, one way or another. Onboarding and training is challenge #1 in the Age of AI.
A quarterly Zoom QBR with nine people on mute doesn’t count.
The CCO who works is:
- In the customer’s office the first week.
- They hear the complaint the customer would never put in a ticket or an NPS survey.
- They find out the champion is leaving before the renewal is at risk. They see the competitor’s logo on the whiteboard.
- Activating customers themselves, at least when they start
The CCO who stays home manages to a health score. Health scores stay green right up to the churn notice.
Agent deployments fail if the CCO doesn’t drive massive improvement here. A health score isn’t that.
Why the Rule Holds to at Least $100M and Really $250M ARR
Three reasons.
- The playbook from the last one doesn’t magically work at your startup. In fact, it almost never does.
- The best way to work for the best. That means folks doing it, and leading from the front. The mediocre are find with a hand-offs manager that just wants to keep a tight ship.
- It’s too competitive. The world changes too fast in the Age of AI.
At a huge public company with ten layers, maybe the job really is allocating capital and people. But most founders are a long way from that company and hire as if they’re already there. They bring in the exec from the $2B company who hasn’t touched the work in a decade. It fails.
Teams Got Smaller in 2026, Which Leaves Even Less Room
We run SaaStr with 3 humans and 20+ AI agents. Plenty of B2B + AI startups are getting to $10M and $20M ARR with a fraction of the headcount that used to take.
When a function is four people and a set of agents, there’s no layer of managers for an exec to manage. The exec does the work and directs the agents doing the rest, or there’s no job there.
Four Questions to Ask Before You Make the Offer
- CRO: “Walk me through the last deal you personally closed. When was it?”
- CTO: “Show me the last thing you shipped yourself.”
- CMO: “What’s the last campaign you ran yourself? How did it perform?”
- CCO: “Which customers did you visit in person last month, and what did you learn that wasn’t in the CRM?”
A vague answer or an old one tells you what you need to know. Then confirm it in references. Ask the people who worked for them when they last saw this person do the work.
And you know this, but it doesn’t get better once they start. It gets worse.
Please Trust Me. Don’t Hire These Ones. No Matter Where They Worked Last
More than half the founders I’ve invested in and worked with have made this mistake. Maybe 95%. Especially when their last company was a well known B2B brand.
If they don’t do it themselves, they will fail. 100% of the time. No matter how nice they are. No matter how beautiful their flow charts are, and no matter how patented their “process” is.
Especially not now. There just isn’t time.
