I started selling in 1994. I was a kid. Since then, I’ve been a rep, a manager, an RVP, a CEO. I’ve hired and fired sales leaders. Now I’m the Head of Enterprise Sales at Dify. I still coach select founders, CEOs, CROs, and other executives. Just not our competitors. Across 30 years and a dozen revenue roles, one thing has become apparent to me. Most sales leaders have short careers.
The average tenure of a Chief Revenue Officer today is between 18 and 25 months. Harvard Business Review reports the CRO average at 25 months, among the shortest in the C-suite. Analysis of 14,000 executives by Pave puts the median at 1.8 years for both CROs and CMOs, with 32 percent annual turnover. Gong’s research on tech VP Sales tenure shows it has fallen from roughly 26 months to 19 months over a seven-year stretch. Compare that to CEOs at 4.3 years and CTOs at 3.7. Go-to-market leadership has the shortest tenure of any executive function in the company, by a wide margin.
The official explanation is that sales leaders miss their number. Technically true. And it’s almost never the actual reason.
The actual reason, and I’m quite opinionated on the topic, is that most companies are not built to support the work that produces revenue. They are built to support the work that looks like revenue is being produced. The gap between those two things is where every sales leader I have known, including the ones I respect most, has eventually run out of road.
What Companies Actually Measure
Walk into almost any B2B sales organization and look at what is on the dashboard.
Meetings booked. Opportunities created. Pipeline coverage ratio. Demos delivered. Outbound activity. MEDDIC or MEDDPICC fields populated. Stage progression velocity. Forecast call accuracy at the deal level. Weekly hygiene scores.
Every one of these is countable. Every one of these can be reviewed in a weekly pipeline meeting and produce the sense that real work is being done. Every one of these can be reported up to a board with a chart that trends in a direction. Not one of those, by itself, produces a closed deal.
What produces a closed deal is the buyer’s willingness to change.
That’s it. Nothing else. The moment when a senior person on the buyer’s side decides that the cost of staying where they are is higher than the cost of doing the work to move. Until that moment arrives, no demo, no proposal, no follow-up, no nurture sequence will move the deal forward. After that moment arrives, almost any execution will close it.
This is not new. Mike Bosworth named it in the 1990s. MEDDPICC literature calls poor pain discovery a massive hidden cost of B2B sales. A piece published on CustomerThink in late 2025 stated plainly that when sales teams are incentivized on activity, salespeople prioritize speed over understanding and rush through discovery to hit their activity targets. A clinical sales firm documented replacing “new meetings per month” with “new cross-functional contacts added per account,” watching pipeline volume shrink and close rate jump 30 percent.
The research has been clear for decades. But the behavior has not changed. And LinkedIn is full of influencers shilling out useless metrics and activities. Why?
Because Pain Discovery Is Uncomfortable
That’s it. Nothing else. Sitting with a prospect long enough to surface what they have not yet admitted to themselves requires the seller to do three things that human beings instinctively avoid.
Ask a question they do not already know the answer to.
Stay silent after the buyer gives any response.
Ask a harder follow-up that makes the cost of the buyer’s current situation real enough that the buyer feels it in the room.
Most sellers will not do this. They retreat to the demo. They retreat to the feature list. They retreat to the follow-up email. These are activities that can be completed without anyone feeling anything. They move the dashboard. They do not move the buyer.
And This Brings Me To The Sales Leader.
A sales leader who has not done the personal work to tolerate this discomfort cannot coach it. They cannot sit in a deal review and watch a rep fail to articulate the buyer’s pain without rescuing them. They cannot push back on the CRO or CEO when the request is “more activity” and the right answer is “deeper qualification.”
So they build the team they can manage. Which is the team that produces the activity dashboard. Which is the team that misses the number. Which is the team whose leader gets replaced in 18 to 25 months.
Three scenarios I have seen
Scenario one. The pipeline review.
A rep is walking the team through a deal in stage three. The economic buyer has not been in a meeting yet. The rep says “they’re really engaged” four times. The manager asks about next steps. The rep says a follow-up demo is scheduled for next Thursday with the original champion. The manager moves to the next deal. The deal stays in stage three for two more quarters. It eventually goes to closed-lost with the reason “no decision.”
What did not happen in that pipeline review. Nobody asked what the buyer was trying to accomplish in their own words, and what it was costing the buyer to not have it today. Nobody made the rep sit in the discomfort of not knowing. Nobody made the manager sit in the discomfort of a rep not knowing. The review rewarded motions and metrics. It did not reward depth.
Scenario two. The QBR with the board.
The CRO presents pipeline coverage at 4.2x. The board nods. Coverage is the headline. Nobody asks how many of those opportunities have a documented, quantified business pain attached to them. Nobody asks the win rate by depth-of-qualification. The CRO has been trained that 4.2x is the answer to the question. When the quarter closes at 60 percent of plan, the diagnosis is “execution issues at the rep level.” Six months later the CRO is gone. The next CRO inherits a 4.2x coverage ratio and the same conversion problem.
Scenario three. The hire who tried to slow it down.
A new VP of Sales joins. Within 90 days they propose narrowing the ICP, killing two-thirds of the pipeline, and rebuilding discovery to surface quantified pain before any deal advances past stage two. Pipeline volume drops 40 percent in the first quarter. The board asks questions. The CEO panics. The VP defends the methodology, points to early conversion improvements, asks to see the year through. They do not get it. They are replaced in Q3 by someone who promises to “rebuild pipeline aggressively.” Pipeline rebuilds. Conversion stays where it was. The cycle continues.
The Discomfort Problem
Most companies have a discomfort problem.
Asking about pain, and the impact of that pain on the buyer, their department, their career, and the overall business, is uncomfortable for the seller. Coaching to depth is uncomfortable for the manager. Forecasting fewer, deeper opportunities is uncomfortable for the CRO. Watching pipeline volume drop while conversion improves is uncomfortable for the CEO. Explaining to the board that quality is going up while quantity is going down is uncomfortable for everyone.
Activity is the escape. Activity lets every layer of the company seem productive without anyone having to feel anything. The price is paid in two places. Buyers do not change. And every 18 to 25 months, the sales leader gets replaced for failing to produce a result the company was never built to produce.
The leaders who break this cycle, the ones I have seen thrive and build revenue teams that hold up over time, have one thing in common. They are willing to be uncomfortable.
They will defend a smaller pipeline in a board meeting. They will let a rep struggle in a deal review. They will ask the buyer the question that makes the room go quiet. They will slow deals ready to sign, because when they win deals, they make sure the buyer actually changes. (Read “renewal”)
This is not a methodology. You cannot install it from a deck. It is a leadership posture. It starts with whether the person at the top can sit in the discomfort themselves, or whether they need the dashboard to tell them everything is fine.
In 30 years of various roles, I’ve gotten comfortable with one thing – discomfort. The teams that win are the ones whose leaders are comfortable with discomfort. Everything else is theater.
And yes, our teams have crushed quotas.
Just ask them.