Is your brand ready for the holiday season—or stuck in the same old cycle?

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In 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.

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Jennie 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.

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If your marketing still thinks like it’s 2019, this episode will challenge your entire playbook.

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Jennie 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.

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• Why performance marketers are embracing brand-building tools like creator partnerships and sonic logos
• How Gen Z and millennials trust creators more than brands—and what that means for strategy
• The difference between polished vs. native content in modern brand storytelling
• Out-of-home as a driver for digital retargeting and campaign amplification
• Why emotional marketing and functional marketing must be balanced
• The “magic brandformance formula” that blends awareness with action
• Planning for Q4: earlier timelines, limited inventory, and smarter holiday messaging
• Why brand marketing needs to prioritize LTV over short-term performance metrics
• What most brands get wrong about awareness, and how to avoid “Blockbuster syndrome”
• How creative testing, speed, and cultural timing win in the modern DTC landscape

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• Rock the Brands
• Jennie Kaylie on LinkedIn
• Glossier subway campaign with digital retargeting
• Spotify Wrapped outdoor campaign
• Brand measurement platforms: Yuca, Google Brand Lift, Meta Brand Lift

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