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The Rainmaker Trap: Why Promoting Your Top Salesperson Can Stall Growth | William Bell

Built to Finish

Release Date: 07/23/2025

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More Episodes

William Bell, Chief Sales Officer at Chief Outsiders and Founder and Chief Executive Officer of Accelerate Consulting, discusses the critical strategies for successfully selling a business. He shares his expert advice for founders, covering everything from maximizing valuation to navigating the intense due diligence process. Discover the common "tricks" sellers attempt, such as manipulating pipelines with non-binding letters of intent, and why honesty is always the best policy to avoid derailing a deal. William and Steven also share their personal experiences as members of the CEO Project, highlighting how an advisory board of peers can help leaders brainstorm solutions and accelerate success.


 

Takeaways:

  • Maximize Your Sale: Hiring a good investment banker is the most important first step a founder can take when looking to sell. To get the highest price, your best bet is to try and sell to a strategic acquirer, who will almost always pay more than a private equity firm.
  • Due Diligence is Deep: Be honest and upfront during due diligence, as acquirers will dig deep and likely uncover any hidden information, such as undisclosed stock transfers or shell companies. Trying to "pull the wool over" a PE firm's eyes is very difficult.
  • The "Second Bite" is Real: Founders have a great opportunity for a "second bite of the apple" by rolling equity forward into the new company. This second payout can realistically be three to four times the multiple on the reinvested money.
  • Avoid the "Rainmaker" Trap: Promoting your top "rainmaker" salesperson to sales manager is a "very big mistake" that stalls growth in many companies. The skillset of a great salesperson is completely different from that of a sales manager, and you lose your best person in the field.
  • The Post-Acquisition Myth: Bill completely disagrees with the idea that a private equity firm will automatically fire a founder CEO within a year. Good PE firms often want the founder to stay and will have honest conversations about their future role before the deal closes.


Quote of the Show:

  • “Being a rainmaker is a completely different skillset than being a sales manager.”


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