The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

How to Evolve as a CMO: Navigating New Markets, Personas, and Business Models with Kady Srinivasan

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Aug 25, 2025

Kady Srinivasan, CMO at You.com, has a rich background leading marketing for Dropbox and Klaviyo. She shares her journey from engineering to marketing leadership, underscoring the importance of adaptability in today's fast-paced environment. Topics include aligning marketing strategies with company goals and effective team management systems. Kady discusses how AI is reshaping marketing roles and the necessity for CMOs to embrace flexibility and innovation. She inspires listeners to reinvent themselves while emphasizing the balance between automation and human creativity.

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ANECDOTE

From Failed Engineer To CMO

Kady transitioned from being a bad software engineer to a marketer and started in B2C before moving to gaming and then tech.
She worked at Dropbox, Klaviyo, Lightspeed and now serves as CMO at you.com, showing a varied career path.

ANECDOTE

How You.com Got Its Domain

The you.com domain was a parting gift from Marc Benioff to CEO Richard Socher because of their past Salesforce relationship.
Kady shares this origin story to explain why the brand has such a memorable domain.

INSIGHT

Storytelling And Job‑to‑Be‑Done Are Core

Kady says the two recurring fundamentals are strong storytelling and connecting product to customer jobs-to-be-done.
These pillars repeat across industries and business models and form job number one for a CMO.

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#276 Career Growth | Dave is joined by Kady Srinivasan, CMO at You.com, an AI-first company building infrastructure for enterprise agents. Kady has led marketing at some of the world’s most recognizable companies, including Dropbox, Klaviyo, and Lightspeed, where she scaled teams, drove massive revenue growth, and navigated ICP pivots. Now, she’s bringing that experience into the fast-changing world of AI.

Dave and Kady cover:

How to evolve as a CMO across industries, personas, and business models
The three core systems CMOs need to scale teams and drive alignment
How AI is reshaping marketing roles, workflows, and the skills future CMOs will need

You’ll walk away with lessons you can apply to your own career, no matter what market or role you’re in.

Timestamps

(00:00) - – Intro
(02:24) - – From engineer to reluctant marketer
(04:58) - – Gaming years and “coolest mom” cred
(07:13) - – The story behind You.com’s domain
(08:52) - – Why she jumped into AI
(11:21) - – Reinventing yourself as a CMO
(13:21) - – Fundamentals that never change in marketing
(15:34) - – Aligning marketing with company strategy
(18:45) - – Pivoting the ICP at Lightspeed
(21:47) - – Lessons on cross-functional alignment
(24:29) - – Letting go to grow as a leader
(27:14) - – Systems every CMO should set up
(34:14) - – Why no single playbook works
(35:55) - – How AI is reshaping marketing roles
(50:35) - – Building an AI-first marketing org and closing thoughts

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