The Enterprise AI Buyer's Real Question in 2026 | Stephen Jenkins, Glean

Stephen Jenkins is Regional VP at Glean, the enterprise AI knowledge platform that grew from $100m to $300m ARR in fifteen months. He covers everything outside the UK across the Nordics, Benelux, Southern Europe, and DACH, and co-founded Sales Heads, an invite-only community for senior sales leaders built around honesty and no bravado.In this episode of The Outside Seat, Mike Tumalty and Stephen Jenkins cover what the enterprise AI buyer is actually asking in 2026, why Glean never brings the product into the first few conversations, what the Sales Heads Amsterdam roundtable revealed about AI and SDR engagement, and why Jim Collins' Good to Great still shapes how Stephen builds operating rhythms across twenty-plus markets.What we cover:The shift in the enterprise AI buyer question: from "what is AI?" to "how do I unlock value without creating risk?"The blueprinting session: how Glean sells to non-technical buyers without leading with the productWhy cold calling is not dead and what the Amsterdam Sales Heads roundtable revealed about AI outreachThe dual perspective of selling AI while using AI to run the commercial operationStructure brings freedom: operating rhythm as the constant across twenty-plus markets and culturesWhy Sales Heads was built: the loneliness of sales leadership and the silence problemGood to Great, pipeline generation, and the desire to be greatAbout Stephen Jenkins:Stephen Jenkins is Regional VP at Glean and co-founder of Sales Heads. His career spans ServiceNow, Jamf, Miro, and Glean. He is based in the Netherlands.LinkedIn: https://www.linkedin.com/in/stevejenkins14/Episode 3 is supported by Flourish, an early-career B2B sales recruitment and training business. If you are hiring sales talent, look at what they do: https://info.helloflourish.com/hire-a...The Outside Seat is a B2B revenue leadership podcast hosted by Mike Tumalty. New episodes every week.InsideNow: GTM diagnostics and commercial due diligence for B2B SaaS. insidenow.io