Episode
297. Why Everything You Know About Sales Is Wrong, with Thomas Waites
- Podcast
- Truth, Lies and Work
- Published
- Apr 30, 2026
- Duration seconds
- 3144
- Processing state
not_requested- Canonical source
- https://traffic.megaphone.fm/HS5343448602.mp3?updated=1777632610
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Summary
Welcome back to Truth, Lies & Work, the award-winning workplace podcast where behavioral science meets workplace culture. Part of the HubSpot Podcast Network, the audio destination for business professionals. If you’re a founder who has built something brilliant but finds the idea of 'selling' it a little bit icky, this episode is for you. Today, we’re joined by Thomas Waites, a fractional Chief Revenue Officer and startup advisor who has scaled multiple companies from seed stage to successful acquisition. Thomas takes a refreshingly contrarian view of sales. He argues that the very traits many founders think disqualify them from sales—honesty, empathy, and a hatred for pushiness—are actually their greatest competitive advantages. 🔥 What we cover in this episode: The "Rainmaker" Reimagined: Why a Chief Revenue Officer (CRO) is about more than just closing deals—it’s about owning the entire customer revenue journey. The Tattoo Bet: The incredible story of how a team culture of "tattoo bets" led Thomas to ink a bull on his shoulder after closing a massive deal with 40,000 Warner Brothers employees. Sales for STEM Founders: How highly analytical, introverted founders can become world-class at sales by treating it like an engineering problem. The 75/25 Rule: Why the best salespeople speak only 25% of the time and how "negative reverse selling" can turn a 'no' into a 'yes' by simply respecting the prospect's boundaries. Building Your Sales Team: Why your first hire should NOT be a VP of Sales or a CRO, and the specific progression founders should follow to scale their revenue. 🧠 Key Takeaways Honesty is a Competitive Advantage: Most prospects expect to be lied to. When you are transparent about what your product can’t do, you build instant, unshakeable trust. Sell to Emotio…