Brand Is a Long Game—Here’s How to Win It (with Jennie Kaylie) | Ep. 21

Is your brand ready for the holiday season—or stuck in the same old cycle?ㅤIn this episode, Charlie Riley and Greg Wise sit down with Jennie Kaylie, CEO of Rock the Brands, to explore the shifting dynamics of DTC branding, where even the most performance-driven marketers are now investing in sonic logos, creator partnerships, and emotional value.ㅤJennie breaks down why today’s consumers expect authenticity over polish, what makes creators more trusted than brands, and how long-term loyalty—not short-term ROAS—defines success. The conversation covers how out-of-home can seed digital campaigns, why most brands live in a bubble, and why your team might need to hit autopilot just to make Q4 count.ㅤIf your marketing still thinks like it’s 2019, this episode will challenge your entire playbook.ㅤ👤 Guest BioJennie Kaylie is the CEO of Rock the Brands, a branding agency focused on helping DTC brands grow through strategy, marketing, customer experience, and innovation. A self-described brand “Swiss Army knife,” Jennie has worked with companies including Wayfair, PwC, Suntory, and Edelman. She brings deep expertise in brand strategy, creative direction, and building emotional value in a crowded market.ㅤ📌 What We CoverWhy performance marketers are embracing brand-building tools like creator partnerships and sonic logosHow Gen Z and millennials trust creators more than brands—and what that means for strategyThe difference between polished vs. native content in modern brand storytellingOut-of-home as a driver for digital retargeting and campaign amplificationWhy emotional marketing and functional marketing must be balancedThe “magic brandformance formula” that blends awareness with actionPlanning for Q4: earlier timelines, limited inventory, and smarter holiday messagingWhy brand marketing needs to prioritize LTV over short-term performance metricsWhat most brands get wrong about awareness, and how to avoid “Blockbuster syndrome”How creative testing, speed, and cultural timing win in the modern DTC landscapeㅤ🔗 Resources MentionedRock the BrandsJennie Kaylie on LinkedInGlossier subway campaign with digital retargetingSpotify Wrapped outdoor campaignBrand measurement platforms: Yuca, Google Brand Lift, Meta Brand LiftㅤLow-Tech, High-Impact Account-Based MarketingIf you’re ready to trade expensive, tech-heavy account-based marketing for a repeatable, revenue-driving ABM program, check out Scrappy ABM. Led by a team of Scrappy ABM experts, they specialize in low-budget plays and programs that deliver high impact—no shiny tools required. Scrappy ABM has built account-based programs that have delivered millions in revenue, and you can build your first successful ABM program with their help.Start with a pilot program or launch an account-based podcast. Learn more at scrappyabm.com. Let's get scrappy.