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

📬 Connect with Al & Leanne

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