How CMOs Are Deploying AI Across Marketing
The Dave Gerhardt Show (from Exit Five)
What failed—and restarted—Three Play's AI effort
Lily recounts earlier failures, why tooling and leadership adoption mattered, and how they refocused efforts.
#353 | Tara (CMO, Optimizely), Julia (Director of AI Adoption, Optimizely), Lily (CMO, Three Play Media), Pejman (CMO, Menlo Security), and Kevin (CMO, CompTIA) join Dave for a live Exit Five session on how real marketing teams are actually using AI right now. Lily shows how she replaced two BDR headcount with a HubSpot prospecting agent and went from an 18% to 46% response rate on inbound leads. Julia walks through how Optimizely's marketing team embedded AI agents directly into their content workflow, from briefing to brand voice checking to traffic monitoring, without anyone having to leave the platform. Pejman shares the framework his team uses to map workflows and find the highest-ROI AI opportunities, plus a custom brand tone tool that turns hours of manual review into minutes. And Kevin talks through what it actually looks like to lead an AI culture change on a small team with limited resources.
Timestamps
- (00:00) - - Intro
- (06:55) - - Guest intros: Tara, Julia, Lily, Pejman, and Kevin
- (12:04) - - Tara on why AI adoption needs an internal owner and how to govern it without squashing enthusiasm
- (15:02) - - Lily: why their first AI initiative failed and what they did differently
- (17:15) - - How Lovable kicked off team-wide AI excitement at Three Play Media
- (19:37) - - Lily's HubSpot prospecting agent: 18% to 46% response rate on inbound leads
- (23:19) - - Julia: embedding AI agents into Optimizely's content workflow
- (31:20) - - Using AI to monitor content performance and auto-assign optimization work
- (33:24) - - Pejman: mapping workflows to find the highest-ROI AI opportunities
- (35:55) - - Building a brand tone checker that scores and rewrites content against brand guidelines
- (39:55) - - Kevin: making AI a mandate on a small team and building a culture of learning
- (44:06) - - Group Q&A: optimizing spend vs. shipping faster, budget shifts, and new KPIs
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