The Billion-Dollar Truck Stop Strategy! with Adrienne Ingoldt, CMO at Pilot Company

On this episode of TOP CMO, host Ben Kaplan speaks with Adrienne Ingoldt, Chief Marketing Officer at Pilot Company—the largest network of roadside travel centers in North America and a key part of Warren Buffett’s Berkshire Hathaway portfolio. Adrienne reveals how she’s leading a monumental shift from a B2B-focused strategy to creating a consumer-first brand that resonates with everyone from professional truck drivers to road-tripping families. Explore the innovative ways Pilot Company is breaking out of a commoditized category, using data-driven personalization, loyalty programs, and emotional storytelling to win over hearts (and wallets). Adrienne shares exclusive insights into building brand awareness in a historically overlooked industry, balancing B2B and B2C priorities, and driving customer loyalty with cutting-edge marketing techniques. If you’re a CMO or marketing leader eager to learn how to create consumer loyalty in competitive markets—or just fascinated by how marketing can transform entire industries—this is an episode you can’t miss.

In this insightful episode of TOP CMO, Jackson Carpenter chats with Dave King, CMO at HeyGen, to explore the cutting-edge world of AI-powered video creation. Discover how Heygen is revolutionizing video production by making it faster, more personalized, and accessible to businesses of all sizes. Dive into the challenges of marketing to a global audience, the impact of AI on content creation, and strategies for building trust and safety in digital storytelling. Gain inspiration from Dave's rich career spanning Salesforce and Asana, and learn how to adapt and thrive in a fast-evolving marketing landscape.

In this episode, we dive into the heart of what makes Ace Hardware a beloved and resilient brand with Kim Lefko, Chief Marketing Officer of Ace Hardware. Kim shares insights into how Ace celebrates 100 years of service and community through initiatives like its new documentary series, which captures heart-warming stories of "Red-Vested Heroes" going above and beyond for their customers. Discover how this co-op retailer keeps a local focus while growing to over 5,000 stores nationwide, stays true to its three pillars of service, convenience, and quality, and continually reinvents its brand to stay relevant in the digital era. Kim’s candid take on customer trust, the power of authenticity, and why staying rooted in a brand's ethos matters—especially in today’s crowded retail space—make this a conversation brimming with lessons for marketers and business leaders alike. Tune in to be inspired by the legacy and future of the “helpful place.”

In this episode of TOP CMO, Ben Kaplan sits down with Rowan Tonkin, CMO of Planful, to discuss the evolving landscape of financial planning and how companies can achieve profitable growth in today’s market. Rowan shares insights on shifting from a "growth at all costs" mindset to a more controlled, sustainable approach. They dive deep into the challenges of staying industry-agnostic while tailoring marketing strategies to diverse personas, and how marketers can foster stronger relationships with CFOs by aligning on commercial and financial metrics. Tune in to explore how Rowan navigates the balance between short-term wins and long-term value in a dynamic business environment.

Join us on TOP CMO as we sit down with Wendy Wu, CMO of SailPoint, to explore her journey from Microsoft to Google and beyond. Wendy shares key insights into navigating the evolving landscape of marketing, the importance of being data-driven, and her experience shaping SailPoint into a leader in identity security. Whether you're interested in SaaS, leadership, or crafting a winning marketing strategy, this episode delivers actionable takeaways for aspiring CMOs and seasoned professionals alike.

In this episode, Eric Hanson, CMO of Mitel, shares insights on repositioning a long-established company to navigate industry shifts and challenge modern market hype. Eric dives into strategies for aligning sales, marketing, and product teams, overcoming the pandemic's impact, and ensuring long-term success in a hybrid business communications landscape. Tune in to learn how to redefine a brand’s story while maintaining core values in a dynamic market environment.

In this episode, Ben Kaplan sits down with Kristen D’Arcy, Chief Marketing Officer at True Religion, to explore how the iconic denim brand reinvented itself. Kristen shares insights on maintaining authenticity, connecting with urban culture, and co-creating with customers to keep the brand relevant. From navigating turnarounds and embracing digital-first strategies to executing 360-degree holiday campaigns, she offers a candid look at how True Religion is resonating with new audiences while staying true to its roots. Tune in to hear about the exciting collaborations, bold moves, and what’s next for this legendary brand.

In this episode of TOP CMO, Jackson Carpenter sits down with Nate Chang, CMO of CycleBar—the world's largest indoor cycling franchise with over 200 locations globally. Nate shares his experience navigating the challenges of maintaining brand consistency while adapting to the unique needs of franchisees. From his days leading the rebrand of Yoga Six to expanding CycleBar's presence, Nate dives into the strategic insights that help franchise marketers empower local owners, stay relevant, and evolve in a competitive fitness industry. Tune in to hear how customer feedback, adaptable marketing, and a strong brand vision have shaped CycleBar’s continued growth and success​.

In this episode of TOP CMO, Ben Kaplan interviews MariCarmen Ribes, Chief Marketing Officer of Kyndryl UK and Ireland, who shares the inside story of how Kyndryl emerged from its IBM legacy to become a bold, independent brand. With over 25 years of experience, MariCarmen dives into what makes the “Kyndryl Way” unique—a culture built on being restless, empathetic, and devoted. She explains how these core values are not just internal principles but are infused into every customer interaction, redefining how Kyndryl builds trust and strengthens relationships post-spin-off. From creating a distinctive identity to implementing a comprehensive account-based marketing strategy, MariCarmen provides a masterclass in modern marketing, leadership, and the power of culture. She also explores Kyndryl’s strategic use of AI, shares lessons learned from navigating damaged customer relationships, and offers her perspective on achieving work-life balance as a leader.

In this episode of TOP CMO, we sit down with Melissa Waters, CMO of Upwork, to explore the evolution of remote work, the power of AI in talent acquisition, and the challenges of rebranding a global freelancing platform. Melissa shares insights on how Upwork is shifting the narrative from a transactional marketplace to a long-term staffing solution, while navigating the rise of AI and maintaining a strong company culture in a remote-first environment. Tune in to hear her strategies for driving brand awareness and fostering a community of innovation and high-quality talent.