#203: Strategy | Why Cookie Cutter Marketing Doesn’t Work with Gurdeep Dhillon, CMO at ContentStack
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 GenerationProven strategies to create urgency and close sales deals in enterprise marketsA glimpse into ContentStack’s team structure and how they plan for growthTimestamps(00:00) - - Intro to Gurdeep (07:01) - - Brand and Audience Marketing (08:13) - - How the Role of Demand Gen is Changing (12:23) - - Brand and Reputation > Lead Generation (17:13) - - How Contentstack is Doing Demand Gen (19:51) - - How to Create Urgency to Win Sales Deals (21:32) - - Making a Good Offer in B2B Marketing (22:48) - - Why Being Bold and Taking Risks is Important in Marketing (28:40) - - Selling Your Vision to Leadership (31:21) - - How Contentstack Has Over 10,000 Global ICP Accounts (36:04) - - Team Structure at Contentstack (41:02) - - Running Marketing and Operating a High-Performing Team (43:18) - - Setting Effective Annual Plans (45:33) - - AI’s Role in Marketing (49:07) - - Closing Thoughts Send guest pitches and ideas to hi@exitfive.comJoin the Exit Five Newsletter here: https://www.exitfive.com/newsletterCheck 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 Customer.io.You know that feeling when you open your inbox, and it’s just… noise? Bad marketing. Spam. Most companies are out here just talking at customers, not talking to them.Marketing messages should do more than just land in an inbox – they should create impact and drive real engagement.Customer.io helps companies send smarter, more personalized messages using first-party data. Their platform enables brands to reach customers at the right time, in the right place, on the right channel—whether that’s email, SMS, push notifications, or beyond.And the best part is that it’s all automated, so you’re not just blasting campaigns and hoping for the best. You’re running a machine that delivers real, human engagement at scale.7,000+ brands already trust Customer.io to make their marketing feel less like noise and more like connection. Join them by visiting Customer.io to get started. ***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