Phase 2 and Beyond: AI as a True Co-pilot

#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

Join 50,0000 people who get Dave's Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Brought to you by:

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.

Consensus - An AI-powered interactive demo platform that lets you put personalized, self-serve demos on your site to turn anonymous researchers into high-intent leads. Learn more at goconsensus.com/exitfive.

Knak - A no-code, campaign creation platform that lets you go from idea to on-brand email and landing pages in minutes, using AI where it actually matters. Learn more at knak.com/exitfive.

Convertr - The enterprise lead data management platform that sits between your lead sources and your CRM, automatically validating, enriching, and standardizing every lead before it touches your systems. Check them out at convertr.io/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