Sales Is King
213: Kevin Bognar | Stripe
Episode Summary Dan sits down with Kevin Bogner along the Chicago River for a candid conversation about his 30+ year sales career: from 18 years at Microsoft to Philips, a CRO stint at a Vista Equity portfolio company, leading global sales at Outreach, and now building the SMB and commercial sales organization at Stripe. Key Topics & Takeaways The "How" vs. The "What" in Sales Kevin's longtime mentor Geoff Nyheim (now a sales professor at DePaul) instilled a foundational principle: the what you do is table stakes. It's the how you do it that differentiates you and advances your career. What the Best Sellers Do Differently Curiosity – Always-on learners who use technology, listen to Gong calls, and constantly sharpen their craft Cross-functional orchestration – The best AEs are "resource brokers," pulling together CSMs, specialists, professional services, and executives to deliver value Multi-threading with sequence in mind – It's not just who you involve, but in what order . Kevin shares how he sent daily stakeholder updates on his biggest deal, scripting who talks to whom and when Authenticity over improvisation – Thinking on your feet includes being comfortable saying "I don't know, but I'll find out" Motivating a Team of 125 Early-Career Sellers Kevin created a program called "Time to Shine": a weekly one-on-one walk to a shoe shine station near the Chicago Merchandise Mart with a top performer nominated by managers. He records a short best-practice interview, shares it on Slack every Friday, and fosters healthy competition. Simple, creative, and effective. The Challenge of Staying Present as a Leader Kevin is candid about his personal challenge: carrying energy from one back-to-back meeting into the next. He's actively working on showing up fully in every conversation, whether it's a FY27 strategy discussion, a deal close, or a career conversation. AI in Sales – Where It's Making the Biggest Impact Strategy and ICP targeting – Using AI to monitor deal patterns in real time (fastest activation, highest usage, fastest close) and identify emerging verticals like GLP-1 distributors, cannabis, and gaming Lookalike prospecting – The best sellers use AI to find the next customer that looks exactly like their last great win Interview signal – Kevin asks every candidate how they're using AI, both to assess their skills and to learn from them Structure vs. Freedom in Sales Methodology Kevin's take: structure matters, especially early in a career. But AI tools like Gong and Outreach are surfacing MEDDIC elements naturally from calls and emails, freeing sellers from checklist-style questioning and enabling more human conversations. Value Selling at Stripe Stripe has a proprietary methodology called The Stripe Way , rooted in value selling. It includes AI-powered tooling that scores calls, emails, and decks against value-selling criteria, generating deal health scores and seller performance dashboards. Notable Quotes "The how we do what we do as sellers is what really advances your career." "The best sellers are resource brokers. They bring all the best people to the table." "I value authenticity. Thinking on your feet includes being able to say 'I don't know.'" "Football teams don't hit the field with just the first play. They hit the field with the entire drive." Note from the Host: This was Sales is King's first on-the-go recording. The iPhone ran out of storage and cut the interview short. Dan plans to reconnect with Kevin for a follow-up episode!
