Make Martech Cool Again: A Conversation with Jason Lyman, Customer.io's CMO

"Marketing to marketers is the dream job, but it makes everything that much more high stakes." – JacquelineIn this Hot Seat episode, Jacqueline sits down with Jason, CMO at Customer.io, to ask a simple question: what would it actually take to make martech cool again? Drawing on stints at Dropbox, BetterCloud, and Microsoft, he unpacks how brand storytelling, design, and experience can turn forgettable software into something people genuinely want to be around, and why so many teams lost that plot after the early cloud-era glory days. From Bob Ross livestreams to "Raiders of the Lost Lifecycle," this is a playbook for injecting swagger back into marketing without sacrificing pipeline, rigor, or credibility.Timestamps00:25 – First Martech tools, Mixpanel obsession, and Jason's weekly grilled cheese ritual06:30 – Shaping brand storytelling: experience at Dropbox, BetterCloud, Microsoft11:43 – What made early Salesforce so magnetic and why Martech lost its spark16:40 – Making Martech cool again: inside Customer.io's Bob Ross, Hot Ones, and Raiders of the Lost Lifecycle concepts and playful brand identity20:00 – What modern marketers actually want from live experiences25:55 – Can mascots, memes, and influencers bring consumer fandom dynamics to Martech?SponsorBrought to you by Hightouch - the leading composable CDP and decisioning platform trusted by brands like Domino's, Chime, and Aritzia. 90% of customers have a real use case live within their first week, delivering world-class personalization at scale. Learn more at www.hightouch.com/msom.Connect & SubscribeSubscribe to Making Sense of Martech wherever you get your podcasts. Follow us on TikTok, LinkedIn, and don't forget to like and subscribe on YouTube.