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

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Dec 10, 2025

In a lively discussion, Jason Lyman, CMO of Customer.io and a marketing veteran from Dropbox and Microsoft, explores how to make martech exciting again. He dives into the art of brand storytelling and the importance of memorable experiences, referencing creative concepts like Bob Ross and 'Raiders of the Lost Lifecycle.' Jason debunks the myth that email is dead, advocates for modern, engaging live experiences, and shares insights on building ambitious, community-focused brands. His enthusiasm for playful marketing strategies is contagious!

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INSIGHT

Email Still Delivers ROI

Email is not dead; personalized, timely email still delivers strong ROI.
Claims email is dead usually reflect poor, generic execution rather than the channel itself.

ANECDOTE

The Weekly Grilled Cheese Ritual

Jason has eaten a grilled cheese every week for over 25 years, usually on Sundays.
His go-to uses grandma's sycamore bread and medium Tillamook cheddar.

INSIGHT

Three Pillars Of Effective Marketing

Best-in-class marketing is customer-centric, metrics-driven, and strategically aligned.
Jason attributes this framework to experiences at Dropbox, BetterCloud, and Microsoft.

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