#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
- (03:03) - – From engineer to reluctant marketer
- (05:37) - – Gaming years and “coolest mom” cred
- (07:52) - – The story behind You.com’s domain
- (09:31) - – Why she jumped into AI
- (12:00) - – Reinventing yourself as a CMO
- (14:00) - – Fundamentals that never change in marketing
- (16:13) - – Aligning marketing with company strategy
- (19:24) - – Pivoting the ICP at Lightspeed
- (22:26) - – Lessons on cross-functional alignment
- (25:08) - – Letting go to grow as a leader
- (27:53) - – Systems every CMO should set up
- (34:43) - – Why no single playbook works
- (36:24) - – How AI is reshaping marketing roles
- (51:04) - – Building an AI-first marketing org and closing thoughts
Send guest pitches and ideas to hi@exitfive.com
Join the Exit Five Newsletter here: https://www.exitfive.com/newsletter
Check out the Exit Five job board: https://jobs.exitfive.com/
Become an Exit Five member: https://community.exitfive.com/checkout/exit-five-membership
***
Today’s episode is brought to you by Walnut.
Why are we pouring all this effort into marketing just to push buyers to a “request a demo” or “contact sales” button?
Come on, today’s buyers don’t want to talk to sales right away. They want to explore your product themselves, see how it works, and understand its value before booking a meeting.
That’s where Walnut comes in.
Walnut empowers marketers and GTM teams to create interactive, self-guided product experiences in minutes. Embed these experiences on your site, in emails, or anywhere in your funnel to let buyers engage on their terms, from awareness to close and beyond.
That's the beauty of Walnut - you're getting a platform that your sales and CS colleagues can use to showcase the product too.
And the best part? You get real intent data—see which features prospects love, where they drop off, and what’s actually driving pipeline. Demo Qualified Leads are the new MQL.
Over 500 companies, like Adobe and NetApp, use Walnut to drive 2-3x higher website conversion rates and 7 figures in pipeline on a yearly basis. So do you want to drive more leads, shorten sales cycles, and actually show your product instead of hiding it behind another typical B2B CTA?
Go check out Walnut.io. And if you tell them Dave from Exit 5 sent you, they'll build out your first demo for free!
