The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

Why Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack

Sep 8, 2025

Gurdeep Dhillon, CMO of Contentstack, brings a wealth of experience from leading marketing roles at top tech firms. He discusses the evolving landscape of demand generation, stressing the shift towards prioritizing brand and reputation over mere lead generation. Gurdeep reveals how urgency can close enterprise sales and emphasizes the need for bold marketing strategies. He also dives into Contentstack's innovative team structure and the transformative role of AI in enhancing marketing efficiency and creativity.

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INSIGHT

Audience Marketing Over Volume Content

Audience marketing is content targeted to the people you want to sell to without explicitly trying to sell to them.
Create content people would pay for to build trusted advisory relationships that drive long-term preference.

INSIGHT

Brand Beats Lead Volume

Demand gen evolved from lead volume to account-based, but the core remains brand and reputation.
Buyers decide as accounts, so marketing must build trust across the buying center, not just collect contacts.

ADVICE

Split Tactics For In-Market And Out-Of-Market

Build both demand-capture for the 10% already buying and demand-generation for the 90% out-of-market.
Ensure paid search, analyst presence, and clear website paths exist to win active deals.

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#280 Strategy | 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
(06:51) - - Brand and Audience Marketing
(08:03) - - How the Role of Demand Gen is Changing
(12:13) - - Brand and Reputation > Lead Generation
(17:03) - - How Contentstack is Doing Demand Gen
(19:41) - - How to Create Urgency to Win Sales Deals
(21:22) - - Making a Good Offer in B2B Marketing
(22:38) - - Why Being Bold and Taking Risks is Important in Marketing
(28:57) - - Selling Your Vision to Leadership
(31:38) - - How Contentstack Has Over 10,000 Global ICP Accounts
(36:21) - - Team Structure at Contentstack
(41:19) - - Running Marketing and Operating a High-Performing Team
(43:35) - - Setting Effective Annual Plans
(45:50) - - AI’s Role in Marketing
(49:24) - - Closing Thoughts

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