TheInquisitor Podcast with Marcus Cauchi
AI won't fix your blind spots. But it will help you find them. with Dave Pender and Dan Simmons
Aug 12, 2026 · 1 hr 1 min · 12 segments
Why This Conversation Matters Most conversations about AI in sales are really just conversations about speed. This one isn't. Marcus sits down with Dave Pender and Dan Simmons, co-founders of…
Why This Conversation Matters Most conversations about AI in sales are really just conversations about speed. This one isn't. Marcus sits down with Dave Pender and Dan Simmons, co-founders of YourSalesEdge, to ask a harder question: is AI making salespeople think better, or just making their existing thinking louder? The answer, it turns out, depends entirely on how you use it. About the Guests Dave Pender has spent 27 years in sales and sales leadership, building business development, account management and key account teams across SaaS businesses globally. Dan Simmons has spent roughly 15 years working alongside Dave, with a similar background leading SaaS sales teams. What They Discuss The conversation opens with a genuine disagreement. Dave argues that sales has always been, and remains, a numbers game. Marcus pushes back hard, arguing it's more accurately an evidence game, and that volume without qualification just produces expensive noise. They find common ground: quality of conversation matters more than count, but only once a minimum bar of relevance is met. From there the conversation moves into how AI is actually being used, and misused, in sales. Dan is blunt about the obvious failures: AI-flavoured emails with the prompt still attached, people asking AI to think instead of asking it to help them think. Dave describes voice-dictating full context into AI rather than typing short prompts, and setting a permanent "critical friend" instruction so the tool never simply agrees with him. Marcus introduces the idea of a human-AI-human loop, building on something Dan describes: start with human intent, bring in AI to assist, run an evidence check, and return to human accountability before anything is acted on. It becomes the spine of the episode. They cover the danger of triangulating across multiple AI models and mistaking agreement for proof, given that most large models are trained on overlapping data and carry similar cultural assumptions. And they discuss the discipline of deliberately switching AI off, in Dan's case for days or weeks at a time, to protect the ability to think independently. Practical Takeaways - Feed AI full context by talking to it, not typing at it. A voice memo produces richer, more usable output than a rushed prompt. - Set a standing instruction telling AI to challenge you, not flatter you. Most tools default to agreement unless told otherwise. - Use the human-AI-human loop. Start with a person, bring in AI to assist and stress-test, then return to human judgement before deciding anything. - Ask AI what you missed, both before and after a call. That question does more work than asking it for answers. - Triangulating across multiple AI tools is not the same as evidence. Most models share training data and similar biases. - Run weekly red-teaming exercises with your team, one side attacking a call, one side defending it, to surface what a seller alone never would. - Build in deliberate AI-free periods to keep independent thinking sharp. Memorable Quotes Marcus challenges the framing of sales as a volume exercise, arguing instead that it's about the quality of evidence gathered before a conversation ever happens. Dan is candid about the risk of overreliance, warning that people are using AI to do their thinking for them rather than to sharpen it. Dave admits that at this point, his AI tool knows more about his working life and thinking than the people closest to him do, a comment that says as much about the pace of adoption as it does about the tool itself. Resources Mentioned - YourSalesEdge, Dave and Dan's company: yoursalesedge.co - Dave Pender and Dan Simmons on LinkedIn - YourSalesEdge on YouTube Guest Biographies Dave Pender has led business development, account management and key account teams in SaaS environments globally over a 27-year sales career. He is co-founder of YourSalesEdge and Blind Spots. Dan Simmons has spent around 15 years working alongside Dave in SaaS sales leadership. Based in London, he describes himself as endlessly curious, particularly about how AI can genuinely improve people's working lives rather than simply speed them up. Listen to More If this conversation challenged how you think about AI in your own sales process, explore more episodes of TheInquisitor Podcast, where Marcus Cauchi questions conventional thinking about selling, buying and leadership.
Why This Conversation Matters Most conversations about AI in sales are really just conversations about speed. This one isn't. Marcus sits down with Dave Pender and Dan Simmons, co-founders of…
