297. Why Everything You Know About Sales Is Wrong, with Thomas Waites

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 Emotions, Not Just Logic: While logic supports a purchase, emotions drive it. Avoid "information overload" and focus on the pain you are solving. Hire Junior First: Start with a Business Development Representative (BDR) to fill the pipeline while you, the founder, continue to close. Only bring in a senior sales leader once the process is proven. 🔗 Connect with Thomas Waites – Website: https://twsales.com – Live Call-In Show: https://twsales.com/live-call-in-show/ – LinkedIn: https://www.linkedin.com/in/thomaswaites/ 📬 Connect with Al & Leanne – LinkedIn: https://www.linkedin.com/company/truthlieswork – Al Elliott: https://www.linkedin.com/in/thisisalelliott – Leanne Elliott: https://www.linkedin.com/in/meetleanne – Email: [email protected] – Book a call: https://savvycal.com/meetleanne/chat Mental health support UK & ROI — Samaritans Call 116 123 or visit https://www.samaritans.org UK — Mind Call 0300 123 3393 or visit https://www.mind.org.uk US — Suicide & Crisis Lifeline Call or text 988 or visit https://988lifeline.org Australia — Lifeline Call 13 11 14 or visit https://www.lifeline.org.au Global helplines https://findahelpline.com