Leadership that Sells is a conversation series with founders, CEOs, sales leaders, and operators.
We talk about:
where leadership models quietly break down
how commercial decisions change under constraint
what experienced leaders eventually stop doing
The focus is judgement, not slogans. Each episode is typically about 30-35 minutes of value.
21 September 2026
More revenue doesn’t automatically mean you’ve built a more valuable business. I want to know what you’re keeping, whether it runs without you and whether you’ve done anything more than make yourself a job. Steve...
3 August 2026
One of the biggest mistakes founders make is believing their business will be valued for what it means to them. It won’t. Buyers pay for predictable cash flow and reduced risk, not emotional attachment. That’s...
20 July 2026
Everyone talks about scaling. Far fewer people actually do it. In this conversation with Doug Levy, we unpack what real operational scale looks like. Not adding people because revenue is growing, but building a business...
29 June 2026
Most strategies don’t fail because the idea was wrong. They fail because nobody properly translated the idea into execution. In this conversation with Crispin Thompson, we got into the uncomfortable gap between strategy and results....
22 June 2026
The more senior you become, the more dangerous certainty gets. That’s the idea at the heart of this conversation with Dr Debra Clary. Most leaders are rewarded for having answers. The problem is that eventually...
15 June 2026
Most of the AI conversation is happening at the wrong level. We’re debating tools, prompts and productivity hacks when the real question is much older and much harder: what does it mean to be human?...
17 June 2024
12 January 2023
2 January 2023
22 December 2022
19 December 2022
16 November 2022
6 November 2022
Stop trying to build a basketball team. Your sales force is a team of Olympians. Get the Parallel Team Playbook for leaders of high-autonomy sales teams.
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