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AI is everywhere in sales right now — and most of what people are doing either turns into spam, or it’s so complicated nobody uses it.

In this episode of Makin Mighty: The Challenger Sessions, Simon Greenwood-Haigh speaks with Craig — founder of Cheesies and a commercial operator/consultant turned AI practitioner — about how challenger brands can use AI to sell more without losing their human edge.

We cover:

• why sales is one of the safer career paths in an AI world (and what will actually change)
• the biggest misuse Craig sees: generic inputs leading to generic output
• a practical “start here” setup (Claude Pro, global instructions, connectors, and better prompting)
• how to keep AI outreach human, on-brand, and believable
• what Craig learned building Cheesies: focus on a single audience and spot early traction signals
• what he’d do differently if starting a brand today with AI agents from day one
• Craig’s new venture, The Expedition, helping FMCG leaders integrate AI properly

Link:
www.makinmighty.com

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And if you’ve got a question you’re wrestling with right now (brand, growth, retail, positioning) email it in. We’re collecting real questions from founders and we’ll use those to shape future episodes.

Thanks for listening. See you next time

makinmighty@gmail.com