14. Max Greenbury, Startup GTM at OpenAI - Inside OpenAI's Sales Playbook

Max Greenbury is part of OpenAI's go-to-market team, working the startup side with around 14 later-stage accounts from the UK to Israel and Lithuania. He didn't get there in a completely straight line (although it was quite straight): three years running his own subscription platform for secondhand clothing came first, three years on AWS's startup team, then Google selling into regulated enterprises. In this episode, Max opens up how OpenAI actually sells and why enterprise and startup deals are almost different jobs. Enterprise sales is a stakeholder maze, won by surfacing "unrealized pain" the buyer hasn't named yet. Startups are the opposite: founders are already pushing the models past their limits, so the job becomes optimizing for latency and cost, then routing what's missing straight back to OpenAI's research team. Max also breaks down OpenAI's AI-first culture, where tools like Codex handle data pulls and CRM updates before a human touches them, and why Generative Engine Optimization, showing up as the answer ChatGPT gives when someone asks for a recommendation, is becoming a real go-to-market priority. Five years out, Max thinks AI takes over the admin grind of selling. What it won't replace, he argues, is trust. If you sell into startups or enterprise, or you're figuring out where GEO fits your own GTM strategy, this one's for you.