The Problem
B2B AI startups are scaling fast and hiring experienced CROs, CMOs, and VPs from recognisable companies. The issue: many of these executives never actually built what they claim on LinkedIn. They worked at successful companies, but they did not create the systems or drive the outcomes.
Now add AI to the mix. Jason Lemkin, founder of SaaStr, argues these "Mediocre Recycled" executives are joining AI-first companies without using AI themselves. No workflows with AI agents. No hands-on experience with Claude or ChatGPT beyond casual queries. They cannot demo the product they are supposed to sell.
The result: they run 2019 playbooks at 2026 companies. They hire the wrong teams, burn six to nine months, then add "VP at hot AI startup" to their resume and move on.
The Red Flags
Classic warning signs:
- No CEO-level reference willing to vouch for their work
- Multiple short VP-level tenures (under a year)
- No strong performers who would follow them to a new role
- Lateral moves between similar companies without clear growth motivation
- Zero homework during the interview process
New AI-era flags:
- Cannot name specific AI tools they use daily or workflows they have automated
- Talk about AI in abstractions ("AI-first strategy") without concrete examples of what they have shipped
- Want to hire large teams immediately instead of leveraging AI to do more with less
What This Means for Sales Hiring
Lemkin's broader point: AI is exposing mediocrity across B2B go-to-market. When content, outbound, and even leadership signals are easier to imitate, the bar for differentiation rises. Buyers and investors expect sharper execution.
For founders hiring sales leadership: treat it as a verification exercise. Push for metrics, reference checks, customer calls, and evidence the candidate can build in a new environment. A VP who has never used an AI SDR tool or pipeline automation will run your revenue org like it is 2021.
The pace is three to five times faster than traditional SaaS. Product changes weekly. Leaders who cannot keep up do not just underperform, they actively slow you down.
Practical Takeaways
- Have the best current VP in that role you know interview the candidate
- Ask what specific AI tools they use and what they have shipped
- Look for evidence of building teams and systems from first principles, not just repeating patterns from a famous employer
- If they fumble on hands-on AI usage, they will struggle at an AI-native company
This is not about technical skills. It is about whether a leader can prove they have driven measurable outcomes and adapted to new environments. In AI, that test is harder to fake.