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
• (07:33) - - Brand and Audience Marketing
• (08:45) - - How the Role of Demand Gen is Changing
• (12:55) - - Brand and Reputation > Lead Generation
• (17:45) - - How Contentstack is Doing Demand Gen
• (20:23) - - How to Create Urgency to Win Sales Deals
• (22:04) - - Making a Good Offer in B2B Marketing
• (23:20) - - Why Being Bold and Taking Risks is Important in Marketing
• (29:45) - - Selling Your Vision to Leadership
• (32:26) - - How Contentstack Has Over 10,000 Global ICP Accounts
• (37:09) - - Team Structure at Contentstack
• (42:07) - - Running Marketing and Operating a High-Performing Team
• (44:23) - - Setting Effective Annual Plans
• (46:38) - - AI’s Role in Marketing
• (50:12) - - 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

***
This episode of the Exit Five podcast is brought to you by our friends at Paramark. You’ve heard it before – every B2B marketer’s top pain point is marketing attribution. It’s complicated, messy, and too often leads to fights with your CRO over whose lead deserves credit.

That’s where Paramark steps in. Their platform makes it simple to understand what’s driving results (and what isn’t) with tools like marketing mix modeling and incremental testing. No more relying on outdated click attribution or chasing UTM links. Instead, Paramark gives you actionable insights across channels, campaigns, and geographies to help you grow.

Paramark's founder & CEO Pranav has been in your shoes as a B2B marketer. He’s so passionate about solving this problem, he’s offering listeners a free brand assessment. Pranav will personally analyze your brand’s performance and share his insights—an opportunity you don’t want to miss.

Slots are limited, so act fast. Head to paramark.com/brand-consult to claim your spot. Trust us, this is worth your time.

***

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