"Marketing to marketers is the dream job, but it makes everything that much more high stakes." – Jacqueline

In 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.

Sponsor

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Timestamps

00:25 – First Martech tools, Mixpanel obsession, and Jason's weekly grilled cheese ritual

06:30 – Shaping brand storytelling: experience at Dropbox, BetterCloud, Microsoft

11:43 – What made early Salesforce so magnetic and why Martech lost its spark

16:40 – Making Martech cool again: inside Customer.io's Bob Ross, Hot Ones, and Raiders of the Lost Lifecycle concepts and playful brand identity

20:00 – What modern marketers actually want from live experiences

25:55 – Can mascots, memes, and influencers bring consumer fandom dynamics to Martech?

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Questions: https://themartechweekly.com/podcast/question/

Confessions: https://themartechweekly.com/podcast/confession-corner/ 

Reddit: https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/

Production Credit: Edited and produced by @the32collective_ / https://www.the32collective.co/