How to Lead Marketing Through the AI Shift with Bill Glenn (SVP of Marketing at Esper)

#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 (02:45) - What Esper does and why software powering hardware matters (05:30) - Why AI feels like the early internet shift (07:20) - Leading with curiosity instead of pretending to be an AI expert (10:00) - Why AI adoption is a behavior change problem, not a tools problem (12:00) - How Esper is rolling out AI with guardrails across the company (17:45) - Why “boring AI” that saves time matters most (19:00) - Phase 1 vs Phase 2 AI adoption in marketing teams (29:10) - AI, mentorship, and preparing the next generation of marketers (41:55) - Leadership advice for first-time CMOs and VPs (47:00) - Final takeaways and wrap-up Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletterLearn more about Exit Five's private marketing community: https://www.exitfive.com/***Brought to you by:Zoom Webinars & Events – The virtual event platform built to help B2B marketers run webinars that actually drive pipeline, with branded registration pages, live engagement features, and built-in tools to repurpose sessions into clips and content. Learn more at zoom.com/exitfive.Customer.io - An AI powered customer engagement platform that help marketers turn first-party data into engaging customer experiences across email, SMS, and push. Learn more at customer.io/exitfive.Vector - A contact-level ads platform that lets you build audiences from actual people on your site, clicking your ads, and checking out your competitors. Learn how to build an ABM program that scales at vector.co/exitfive.Join us in Stowe, Vermont for Drive 2026 - three days away from your desk to learn what's working in B2B marketing from the people who are actually doing it. Grab your ticket at exitfive.com/drive.Walker Sands - An integrated B2B marketing and growth services agency that helps marketing leaders turn strategy into measurable business impact through their Outcome-based Marketing model. Learn more at walkersands.com/exitfive.***Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.They give you unlimited podcast editing and strategy for your B2B podcast.Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.Visit hatch.fm to learn more