You’ve seen this movie before. You acquire a $15M ARR B2B SaaS or services firm. The founder is brilliant, charismatic, and exhausted. They are personally involved in 80% of closed-won deals. Your operating thesis is simple: "Let the founder focus on product/vision, and we’ll hire a ‘real’ VP of Sales to scale revenue."
You pay a recruiter $80k. You hire a polished executive from Salesforce or Oracle. You give them a hefty equity package and a mandate to "double the team."
Twelve months later, you fire them.
Revenue is flat. The new reps haven't ramped. The founder is back in every deal to save the quarter. EBITDA has taken a hit from the severance and failed draw packages.
The failure isn't usually the candidate. It's the sequence. You attempted to hire for Management before you solved for Engineering.
Founders sell on implicit trust and product vision. They don't need a pitch deck; they are the deck. They don't need objection handling scripts; they wrote the code. When you drop a professional sales leader into this environment without a documented process, you are asking them to scale a miracle.
Data from Gong reveals that the average tenure of a VP of Sales has dropped to just 19 months. In the lower-middle market, it’s often closer to 12. This churn isn't a talent problem; it's a playbook problem.
The gap between a founder’s intuition and a sales rep’s execution is where margin goes to die. In a founder-led environment, there is no "standard" deal. Every contract is bespoke, every pricing structure is negotiated on the fly. This works for $10M ARR. It breaks at $20M.
According to research published in the Harvard Business Review, companies with a formal, standardized sales process experience a 28% increase in revenue compared to those relying on ad-hoc methods. Yet, in most Series B/C firms we audit, the "sales playbook" is a folder of outdated PDFs and a Slack channel.
Without a playbook, you face two massive risks:
Before you hire the expensive VP, you need to prove the system works without the founder. This requires a "Sales Engineering" phase. We recommend hiring two "Beta Reps"—mid-level, hungry openers, not closers—and tasking them with breaking the founder’s process.
Their job isn't just to sell; it is to document why they couldn't sell. Every objection the founder overcomes effortlessly must be scripted. Every feature the founder demos must be standardized.
If you are staring at a portfolio company with a stalled sales transition, stop looking for a new VP. Start building the infrastructure that allows a VP to succeed.
You cannot simply ban the founder from sales calls. You must transition them from "Player" to "Coach." Use the framework from The Founder Extraction Playbook: record every call, transcribe the objection handling, and build a library of "Founder Responses." The goal is to turn tribal knowledge into institutional assets.
Don't scale a losing model. Before adding headcount, ensure your LTV/CAC ratios hold up when you load fully-burdened sales costs. Often, founder-led sales look profitable because the founder’s time is "free." Read Stop Buying Growth to recalibrate your targets based on real customer acquisition costs.
Implement strict entry and exit criteria for every pipeline stage. A deal does not move to "Proposal" because the prospect "liked the demo." It moves because BANT (Budget, Authority, Need, Timing) was verified in writing.
The PE Operator’s Mandate: Stop treating sales as a talent issue. Treat it as an engineering issue. You don’t need a Rockstar. You need a Process. Once the machine is built, then you hire the driver.
