What do you get when you mix a 70-year-old legacy brand, Gen Z tax filers, and a reality TV show called Responsibility Island?

An absolute marketing fever dream. And Jill Cress — CMO of H&R Block — is the mastermind behind it. We unpack how she’s giving TurboTax-meets-Gen-Z realness. We’re talking Roblox integrations, bold brand storytelling, and what happens when you challenge a category that’s historically allergic to change.

We cover:

– How H&R Block turned tax season into a cultural moment

– What marketers get wrong about Gen Z (and how to fix it)

– Why AI is useful, but human empathy still pays the bills

– The 4 E’s of customer experience (one of them might make you cry)

This is legacy brand marketing with ✨main character energy.✨Press play. Take notes. Maybe even call your tax pro.

Key Moments:

00:00 Introduction to Jill Cress, CMO of H&R Block

01:49 H&R Block's Legacy and Innovation

13:03 Challenges and Surprises in Marketing

19:45 Responsibility Island: A Bold Marketing Move

25:41 Measuring Success and Future Plans

30:59 Differentiation and Brand Storytelling

33:15 Life Stage Stories and Customer Experience

38:21 The Role of Empathy in Customer Relationships

44:08 AI in Tax Assistance

51:33 The Future of Brand Storytelling

53:43 Advice for Young Marketers

57:02 Relevant or Irrelevant: Lightening Round

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