The Pattern
Jason Lemkin has a blunt take on executive failure: CROs who don't sell themselves fail. CTOs who don't code fail. CMOs who don't market fail. CCOs who avoid customers fail.
His reasoning: it is too competitive, there is too much to learn, even at $150M ARR. Executives who only manage get told what their teams want them to hear. They can't diagnose what is breaking because they are not in the work.
What It Looks Like
The CRO who works is in deals. They take calls with the biggest prospects. They fly out to close. They know the champion's name, the procurement lead's name, and they have accounts where the buyer texts them directly. They run the forecast and they know which parts are real because they were in the room.
The CRO who fails presents pipeline coverage and hiring plans. Ask about a specific deal and the answer is "let me check with the exec on that." Sales slows. Win rates drop. The team gets pressured to squeeze existing customers to make up for it.
The CTO who works ships code regularly, reviews real code, and knows what a team of five can build with AI tooling in 2026. The CTO who fails hasn't committed code in years, can't size teams accurately, and can't spot padded estimates.
The CMO who works writes positioning themselves, rewrites subject lines before send, and knows why last month's campaign missed because they built part of it. The CMO who fails manages budgets and agencies. Pipeline from marketing flattens. The explanation every quarter is attribution.
The CCO who works visits customers in the first week, hears complaints that never make it into tickets, finds out the champion is leaving before renewal risk shows up. The CCO who fails reads health scores. Health scores stay green until the churn notice arrives.
Why It Matters
Lemkin runs SaaStr, a founder-led B2B SaaS media and events business with roughly 24 to 41 people and $4.5M to $5M in revenue. He also runs SaaStr Fund, a seed-stage SaaS investment vehicle with more than $200M under management. In 2026, SaaStr said it was running with three human employees and 21 AI agents, including an AI VP of Revenue. They reported $4.8M in agent-sourced pipeline and $2.4M in closed-won revenue.
That operating model backs his point: executives must stay close to the work. The playbook from the last company rarely works at your startup. The best way to attract the best is to do it yourself. And the market moves too fast for executives who coordinate but don't execute.
For ANZ sales leaders, the implication is straightforward. A CRO should still be able to create and advance opportunities. A CMO should understand demand generation firsthand. A CCO should be in customer conversations. In SaaS, where the CRO coordinates sales, marketing and customer success around one revenue target, a leader who can't demonstrate the core work will struggle to coach teams, diagnose pipeline quality, or separate market problems from execution issues.
Lemkin says the rule holds to at least $100M ARR, possibly $250M. If you are evaluating a CRO role or hiring one, the signal is clear: if they only manage, they can't do the job.