“Don't be afraid to take smart risks. I think if you live in fear, you'll never do the things that make you stand out from the myriad of other awesome people who would want that role.” - Jenna Lebel

Marketing in a low-engagement, heavily regulated industry like insurance demands bold thinking—and Jenna Lebel is delivering just that. As Chief Marketing Officer of US Retail Markets at Liberty Mutual Insurance, Jenna is redefining how brands build emotional connection in commoditized categories. From platform-first creative to data-fueled media strategies and generative AI adoption, she’s leading Liberty’s evolution from legacy insurer to cultural mainstay. In this episode, we explore the tactics and mindset behind the transformation.

Jenna Lebel is the Chief Marketing Officer of US Retail Markets at Liberty Mutual Insurance, overseeing marketing strategy for one of the largest personal lines insurers in the country. With over a decade of experience spanning tech startups and agencies, she’s led Liberty’s push into culture-driven marketing, generative AI adoption, and platform-specific creative. Prior to Liberty, she worked with Likeable and brought an entrepreneurial mindset to corporate brand transformation.

Tune into the latest episode or read the transcript below to learn more. Here are some top takeaways:

The Science Behind Liberty’s Iconic Jingle

You’d have to be living under a rock to not know the “Liberty, Liberty, Liberty…Liberty” jingle. But behind that earworm is a data-driven strategy. Jenna explains how Liberty Mutual rigorously tests every campaign, including its audio branding, for recall, resonance, and long-term impact. The jingle consistently ranks among the top in brand recognition, with Veritonic placing it third in its latest audio logo index. By leaning into memorable brand cues, Liberty has broken through in a category where emotional connection can be hard to earn.

AI’s Four Roles Reshaping Modern Marketing

For Liberty Mutual, AI isn’t just a buzzword, it’s embedded into how the brand operates. Jenna breaks down four key areas where AI is already driving transformation: creative development, media buying, operational efficiency, and consumer behavior insights. From using generative tools for rapid content iteration to real-time targeting and automation, Liberty is leveraging AI to move smarter and faster. But adoption comes with guardrails: quality, ethics, and consumer readiness still lead the way. The takeaway? Brands should experiment boldly, but scale responsibly.

Gen Z, the 300-Foot Scroll, and Platform-First Creative

Gen Z scrolls the equivalent of 300 feet of content every day, so how do you get them to stop and engage with an insurance brand? Jenna shares how Liberty Mutual shifted its strategy from just “being on platforms” to designing content for them. Whether filming iPhone-style videos with Doug for TikTok or partnering with creators like Jo Steele, it’s about meeting Gen Z where they are, with content that feels native, relevant, and scroll-stopping.

The Mindset Shift from Marketer to CMO

Becoming a CMO isn’t just about mastering campaigns, it’s about connecting marketing to the business. Jenna emphasizes the importance of knowing your company’s KPIs, speaking the language of the C-suite, and bringing the voice of the customer into every room. At the same time, creative problem-solving and active listening are the soft skills that make hard decisions easier. Her approach proves that true marketing leadership blends rigor with empathy.

Career Advice Built for the AI Era

As the next generation enters a workforce shaped by AI and uncertainty, Jenna offers timeless advice: master creativity, analytical thinking, communication, and relationships. She urges young professionals to embrace fear as fuel because saying yes to unfamiliar opportunities often leads to the biggest growth. “Don’t be afraid to take smart risks,” she says, reminding us that in a crowded field, boldness is what makes you memorable.