The Exit Five CMO Podcast: Why Cookie Cutter Marketing Doesn’t Work

Guest: Gurdeep Dhillon, CMO at ContentStack
Host: Dave Gerhardt
Release Date: September 8, 2025
Episode Theme:
A candid, insightful deep-dive into why modern enterprise B2B marketing must move beyond formulas and templates, featuring Gurdeep Dhillon’s hard-won experience and philosophy: marketing is a memory and reputation game, not just a lead-gen engine. Gurdeep details his account-based, brand-first approach at ContentStack, the importance of risk-taking for CMOs, and practical frameworks for running a high-impact team.

Main Themes

• Why Marketing Is About Memory, Reputation, and Brand – Not Just Leads
• Authentic Content and Breaking Through the ‘Sea of Noise’
• The Evolution from Demand Generation to Account-Based Strategy
• B2B Offers and Promotions: Beyond B2B "Taboos"
• Building, Structuring, and Operating a Modern Marketing Team
• Agility, Risk-Taking & Moving Away from Cookie Cutter Approaches
• Practical AI Use Cases for Marketers
• Internal Selling: Educating Leadership, Board, and C-Suite

Key Discussion Points & Insights

Gurdeep’s Career Flyover (02:57–04:20)

• 13 years at SAP, ending up leading marketing for their CX business (Marketing Cloud, Sales Cloud, etc.)
• Moved to Marketo to run Demand Gen (acquired by Adobe), then to Adobe (Marketo & Magento) and Zora (subscription management/fintech).
• Recently returned to martech as CMO at ContentStack, excited to market to “his ICP.”

Educational Content Still Matters, but It's Harder Now (05:01–07:20)

• Old vs. New Content Era:
  • Early days: Vendor content (e.g., HubSpot, Marketo) became formative for many marketers due to lack of alternatives.
  • Now: “The cost to create mediocre content is now zero... which isn’t great for anything other than SEO optimization.” (Gurdeep, 05:20)
• Imperative for Exceptional Content:
  • “The only way to rise above the noise...with AI making everything worse...is authentic, relevant content that really does create...a trusted kind of advisory relationship.” (Gurdeep, 06:12)
• Audience Marketing > Content/Brand Marketing:
  • Gurdeep reframes it as “audience marketing,” aiming for “brand relevancy” with the right people at the right accounts.

Modern Demand Generation: It’s Actually About Brand (08:28–13:13)

• Lead Gen Era is Dead:
  • Legacy playbook: “It was all in pursuit of an MQL...lead gen wasn’t the thing. It was brand all along.” (Gurdeep, 11:49)
• Account & Reputation Focus:
  • “Our job as marketers is to make sure that our ICP...knows who we are, believes we are awesome, and engages with us with great content. That produces demand.” (Gurdeep, 12:29)
• Dave’s Summary:
  • “Do people know you exist? Do they believe you can solve their problems?...When they are ready to buy, they’re going to raise their hand.” (Dave, 12:44)

“Demand Capture” vs. Generating True Demand (15:23–19:41)

• Stages of Awareness are still foundational but only a small % of your audience is “in-market” at any time (5–10%).
• The rest require long-term brand and reputation work. “That’s not generating new demand. It’s the 90% out of market I care about for the long game.” (Gurdeep, 15:54)
• ContentStack Overview: Modern CMS platform for omnichannel content experiences and digital experience platforms (DXP).
  • “Headless CMS” explained for non-technical audience (17:50).
• The challenge: creating urgency content for out-of-market prospects vs. capturing short-term demand.

Creating Urgency: Offers & Incentives in B2B (19:41–22:39)

• Tangible Campaign: “Retire the Legacy” – an offer to cut CMS contract in half for customers switching from legacy vendors (Adobe, Sitecore, Oracle). “It’s actually going really well because people are already thinking about it...a catalyst for moving quicker.” (Gurdeep, 19:44)
• Dave and Gurdeep debate why B2B has shied away from classic offers/discounts: “Psychologically, a hundred percent, we should be leaning into these more B2C-like tactics...if we’re going to do audience marketing, we’re marketing to people.” (Gurdeep, 22:31)

The Importance of Risk-Taking & Rejecting Cookie Cutter Marketing (22:48–23:57)

• “I don’t want to do cookie-cutter marketing. A, it doesn’t work. B, how are you going to fight?...There’s no world where I’ll put a dent in this market by playing it safe.” (Gurdeep, 22:54)
• Being bold unlocks risk-taking, trying new things, and, if it fails, “at least we try.”
• “Today’s B2B CMO has to be bold to make a difference.” (Gurdeep, 23:56)

Marketing Is a Memory Game: Standing Out in a Crowded Field (26:26–28:39)

• “Marketing is a game of attention.” (Dave, 26:26)
• “Marketing is a memory game. Whoever plays that game the best...in a crowded space...if you suck at that, you’re done.” (Gurdeep, 27:39)
• “Seventeen-email nurture sequences are an annoyance game—not a memory game.” (Gurdeep, 28:21)

Internal Selling: How to Get Buy-in for Brand/Account-Based Focus (28:39–34:18)

• Convincing CEO, C-suite, board, finance requires a new story: “Show me a company with a pipeline problem, and I’ll show you a company with an awareness problem.” (Gurdeep, 30:44)
• Gurdeep moved ContentStack to an account-based measurement/funnel, tracking targeted accounts across stages from Unaware → Aware → Engaged → Pipeline.
• “Marketing owns the pipeline, full stop.” Agreement and definition aligned with sales and partners—no more MQL battles/attribution fights, only customer/account outcomes. (33:22–34:18)

Building the Modern Marketing Team (36:21–41:22)

• Team Structure:
  • Goal: ~70 people (growing, including a team in India).
  • Four Functions:
    1. Product, Solution & Brand Marketing
    2. Integrated Marketing (content, campaigns, customer)
    3. "Earned Media" (social, PR, influencer—title tbd)
    4. Digital Operations (web, MOPS, analytics, prospecting ops)
  • Global/corporate events and regional alignment handled via a “global marketing” team
• “I’m making it up” – Organize around jobs to be done, not legacy org charts (Dave, 38:14)
• Each function has a single leader; company is remote-first

Marketing Operating System: Planning & Agility (41:22–45:33)

• Planning Cadence:
  • Biannual cross-functional “theme alignment” meeting drives major campaigns for next six months (marketing, sales, product, partners aligned)
  • Quarterly written marketing plans flow from theme priorities
  • Leave space for agility: “Retire the Legacy” offer went from idea to launch in 10 days
  • Annual view for big rocks/budget, but not granularly planned: “90% of the time, you’ll look back and see you did only 40% of what you planned.” (Gurdeep, 43:55)
  • “Focus on big rocks and agility. Don’t waste time trying to over-plan the year.” (Gurdeep, 45:14)

AI’s Role in Marketing: Automation and Speed, Not Just Content (45:33–49:11)

• AI is transforming execution, enabling faster, full-campaign launches and creative focus.
  • “You’re not gonna wait three weeks for a video animation—AI will do that. Humans focus on high-value creative and strategy.” (Gurdeep, 48:09)
• AI as a prospecting and ICP research force multiplier (tools like Klay, Keyplay).
• It’s imperative for teams to be “AI first” where possible.

Memorable Quotes & Moments

• “Lead gen wasn’t the thing. It was brand all along.” (Gurdeep, 11:49)
• “Show me a company that has a pipeline problem and I’ll show you a company that has an awareness challenge.” (Gurdeep, 30:44)
• “Marketing is a memory game. Whoever plays that game the best...if you suck at that, you’re done.” (Gurdeep, 27:39)
• “Psychologically, a hundred percent, we should be leaning into these more B2C-like tactics...We’re marketing to people.” (Gurdeep, 22:31)
• “Cookie cutter marketing doesn’t work. Being bold is a prerequisite for us achieving our goals.” (Gurdeep, 22:54)
• “Marketing owns the pipeline, full stop.” (Gurdeep, 33:22)

Segment Timestamps

| Segment | Timestamps | |-------------------------------------------------|----------------------| | Introduction & Career Recap | 01:26–04:20 | | Content Marketing Then vs. Now | 05:01–07:20 | | Demand Gen’s Evolution | 08:28–13:13 | | Brand, Reputation & Demand Capture | 15:23–19:41 | | Creating Urgency with Offers | 19:41–22:39 | | Boldness & Rejecting Templates | 22:48–23:57 | | Memory & Reputation Game | 26:26–28:39 | | Organizational Buy-In & Account-Based Approach | 28:39–34:18 | | Marketing Team Structure | 36:21–41:22 | | Planning & Agility | 41:22–45:33 | | AI and the Future of Marketing | 45:33–49:11 |

Takeaways For Marketers

• Never mistake tactical lead gen for enduring marketing impact—brand and reputation are the real drivers.
• “Audience marketing” is a modern frame for relevance and brand-building in an AI-noisy world.
• Risk-taking and bold initiatives (not cookie-cutter tactics) are non-negotiable to disrupt and win, especially against giants.
• B2B can—and should—embrace incentives, offers, and B2C tactics to drive urgency, as long as they’re authentic and on-brand.
• Align your team structure to your unique jobs-to-be-done, not templates.
• Internal storytelling to your CEO, board, and peers is as critical as market-facing campaigns.

Listen if you want a practical, straight-talking view of how to build modern B2B pipelines through brand, not MQLs, scrappy creativity, and boldness.