In this episode, Dave is joined by Gurdeep Dhillon, CMO of Contentstack. Gurdeep has built an impressive career leading marketing at some of the biggest names in enterprise software, from SAP to Adobe, Marketo to Zoura. Now at Content Stack, he's challenging conventional B2B marketing wisdom in rethinking how enterprise companies should approach demand generation and brand building. In this conversation, Dave and Gurdeep dive deep into why marketing is ultimately a game of memory and reputation, not just lead generation.
Dave and Gurdeep cover:
- The role of Demand Gen in 2025 (and what's changed)
- Why Brand and Reputation should be prioritized over Lead Generation
- Proven strategies to create urgency and close sales deals in enterprise markets
- A glimpse into ContentStack’s team structure and how they plan for growth
Timestamps
- (00:00) - - Intro to Gurdeep
- (06:50) - - Brand and Audience Marketing
- (08:02) - - How the Role of Demand Gen is Changing
- (12:12) - - Brand and Reputation > Lead Generation
- (17:02) - - How Contentstack is Doing Demand Gen
- (19:40) - - How to Create Urgency to Win Sales Deals
- (21:21) - - Making a Good Offer in B2B Marketing
- (22:37) - - Why Being Bold and Taking Risks is Important in Marketing
- (28:23) - - Selling Your Vision to Leadership
- (31:04) - - How Contentstack Has Over 10,000 Global ICP Accounts
- (35:47) - - Team Structure at Contentstack
- (40:45) - - Running Marketing and Operating a High-Performing Team
- (43:01) - - Setting Effective Annual Plans
- (45:16) - - AI’s Role in Marketing
- (48:50) - - Closing Thoughts
Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/
***
Today's episode is brought to you by Knak.
Email (in my humble opinion) is the still the greatest marketing channel of all-time.
It’s the only way you can truly “own” your audience.
But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever.
That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.
- Frustrated by clunky email builders? You need Knak.
- Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
- Big team making it hard to collaborate and get approvals? Definitely Knak.
And the best part? Everything takes a fraction of the time.
See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.
***
Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.
- They give you unlimited podcast editing and strategy for your B2B podcast.
- Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
- Visit hatch.fm to learn more
