In this episode of Beyond the Billboard, hosts Charlie Riley and Greg Wise welcome Chantelle Rapport, CMO and EVP of Growth at Upstart, to discuss the evolving landscape of brand and performance marketing. They explore how brand extends beyond marketing campaigns to encompass every customer touchpoint, why the separation between brand and performance is artificial, and strategies for measuring long-term brand investments.

Best Moments:

• (00:50) Introduction to Upstart, an AI marketplace connecting borrowers with lenders
• (02:28) Chantelle’s belief that brand and performance marketing are interrelated, not separate
• (04:50) Internal marketing’s role in brand building across the entire organization
• (07:44) Navigating conversations with CFOs about investing in brand marketing
• (12:48) The scrutiny marketers face compared to other business functions
• (16:42) How consumer behavior is changing, leading to digital marketing fatigue
• (20:40) The impact of AI on search and consumer research behaviors
• (23:44) The resurgence of creativity in marketing and its importance in brand building
• (25:09) How AI and data will enhance traditional creative marketing approaches

Guest Bio

Chantelle Rapport is the Chief Marketing Officer and EVP of Growth at Upstart, an AI-powered lending platform that uses over 1,500 variables in its underwriting process to expand access to credit. With a self-described “nontraditional” marketing background that gives her a more analytical perspective, Chantelle oversees brand marketing, performance marketing, creative, and growth product at Upstart. She believes in taking a holistic approach to brand building that spans every customer touchpoint and experience.

“Mobile ads with real-world measurement.” That’s the core of what James Heller created with Wrapify, the out-of-home platform that wraps rideshare and delivery vehicles in brand messaging — and makes it measurable.

In this episode of Beyond The Billboard, Greg Wise, Co-founder of OneScreen.ai, and Charlie Riley, OneScreen’s Head of Marketing, talk with James about turning everyday drivers into moving billboards, Wrapify’s evolution from an idea to a nationwide platform, and how it’s challenging traditional perceptions of OOH.

James shares how he went from running global digital marketing for a cloud division of a Fortune 50 company to cashing out his 401(k) to make the Wrapify vision real. He breaks down why Wrapify’s success isn’t just about the cars — it’s about attribution, media measurement, and the ability to retarget based on physical ad exposure. If you’ve ever wondered what happens when creative marketing meets hard data, this one’s for you.

James Heller is the CEO and Founder of Wrapify, the nation's leading rideshare and mobility advertising platform. He’s a digitally native marketer who previously led global digital marketing for a cloud division of a Fortune 50 company. With Wrapify, he built a way for brands to scale out-of-home across rideshare and gig delivery vehicles, paired with data visualization, attribution, and retargeting capabilities.

LinkedIn Profile

• How Wrapify turns Uber, Lyft, DoorDash, and Instacart vehicles into mobile ad platforms
• Why brands use Wrapify not just for the cars but also for measurement and attribution
• The origins of Wrapify and why James left a Fortune 50 job to build it
• Challenges in traditional out-of-home: “great for top-of-funnel, hard to measure”
• The rise of the gig economy and the gap James saw in OOH advertising
• Using real-world exposure to trigger retargeting

James Heller

Wrapify

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Brand is not simply a logo.

It’s the irrational reason people choose you over your competition. That’s the mindset Preston Rutherford brings to Beyond the Billboard in this informative conversation with hosts Greg Wise, Co-founder of OneScreen.ai, and Charlie Riley, OneScreen’s Head of Marketing.

Preston—widely followed on LinkedIn for his brand-building insights—breaks down how Chubbies disrupted men’s apparel and why the obsession with performance marketing has led many brands astray.

This episode is a CFO-friendly argument for why brand marketing is a smart investment. Preston shares how branded search, contribution margin, and organic revenue serve as real business metrics—not soft ideas. He challenges marketers to master their P&L, think in terms of incremental revenue, and measure what really drives long-term, resilient growth, not just immediate revenue.

If you’ve ever struggled to explain brand marketing value to a CEO or CFO, this episode is the blueprint.

This episode is brought to you by OneScreen.ai

Preston Rutherford is a co-founder of the breakout brand Chubbies, a company built around the idea of weekend apparel that flipped the script on men’s fashion. From startup roots to a nine-figure exit, his journey blends brand-first intuition with performance-era insights. Today, he creates educational content for marketers on LinkedIn and is building Marathon—a measurement tool designed to quantify the real value of brand.

LinkedIn: https://www.linkedin.com/in/prestonr/

• Why “brand marketing” is actually the irrational reason people make buying decisions
• How Chubbies built a cult favorite by challenging the serious, cargo-shorts norm
• Why marketers must understand every line of their company’s P&L
• How branded organic search and direct traffic signal a strong brand
• Why contribution margin—not ROAS—is the CFO-approved way to measure success
• How digital ads have turned into "wacky, wavy inflatable tube men" and what to do about it
• The myth of a short-term drop when investing in brand—and what’s really happening
• How investing in brand reduces discounting and increases resilience in a crowded market

• Preston Rutherford’s LinkedIn
• Marathon

Did you enjoy today’s episode? Make sure to hit the subscribe button so you never miss an update! If you found this conversation insightful, share it with a fellow marketer who should think more about out-of-home advertising. For more insights and tips, connect with us on LinkedIn!