Leading with Curiosity Over Expertise

#328 | Jess Lytle is joined by Bill Glenn, SVP of Marketing at Esper, for a conversation about what it actually looks like to lead a marketing team through the AI shift. They talk about why most teams are still figuring AI out, how leaders should think about adoption beyond just tools, and why curiosity and experimentation matter more than having the “right” answers. Bill also shares how Esper is rolling out AI across the company with guardrails, the internal process they use to evaluate new tools, and why the biggest opportunity right now is using AI to eliminate busywork and unlock better thinking.

Timestamps

• (00:00) - Why AI feels overwhelming for marketing leaders
• (05:00) - What Esper does and why software powering hardware matters
• (07:45) - Why AI feels like the early internet shift
• (09:35) - Leading with curiosity instead of pretending to be an AI expert
• (12:15) - Why AI adoption is a behavior change problem, not a tools problem
• (14:15) - How Esper is rolling out AI with guardrails across the company
• (20:00) - Why “boring AI” that saves time matters most
• (21:15) - Phase 1 vs Phase 2 AI adoption in marketing teams
• (32:46) - AI, mentorship, and preparing the next generation of marketers
• (45:31) - Leadership advice for first-time CMOs and VPs
• (50:36) - Final takeaways and wrap-up

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