"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 Brought 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 <a href= "https://www.google.com/search?q=https://www.hightouch.com/msom">www.hightouch.com/msom</a>. 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? Connect & Subscribe Subscribe to Making Sense of Martech wherever you get your podcasts. Engage with the community on Reddit and follow Making Sense of Martech on LinkedIn, and don't forget to like and subscribe on YouTube. Leave a review, share with your team, and send us your questions and confessions. We may feature you in an upcoming episode! Questions: <a href= "https://themartechweekly.com/podcast/question/">https://themartechweekly.com/podcast/question/</a> Confessions: <a href= "https://themartechweekly.com/podcast/confession-corner/">https://themartechweekly.com/podcast/confession-corner/</a> Reddit: <a href= "https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/"> https://www.reddit.com/r/MSoMPodcast/comments/1morng8/office_hours_questions/</a> Production Credit: Edited and produced by @the32collective_ / <a href= "https://www.the32collective.co/">https://www.the32collective.co/</a>

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