What does it take to keep a 40-year-old brand rooted in nostalgia relevant in a rapidly evolving, tech-driven world?

In this special episode recorded live from the X4 Summit in Salt Lake City, I sit down with Maggie Stafford, Vice President of People Insights at Hagerty, to explore how a company best known for classic car insurance has become a technology-enabled, community-powered lifestyle brand for auto enthusiasts.

From cloud-based transformation to one-on-one customer experiences, Maggie shares how Hagerty is modernizing its approach to customer and employee engagement—while staying true to its mission to "save driving."

We discuss the evolution of Hagerty’s digital experience, including their $20 million investment into a modern tech stack, designed not only to improve operational efficiency but also to meet growing member expectations.

Maggie also gives a behind-the-scenes look at how the brand’s culture—one where employees learn to drive stick and take collector cars for a spin—shapes everything from customer service to product development.

You'll hear how community remains the beating heart of the business, with more than 850,000 Hagerty Drivers Club members connecting at grassroots events and exclusive experiences like the Festival of the Unexceptional and Amelia Island Concours. We also explore how Hagerty is using data and insights to prepare for the future of car culture, at a time when automation, electrification, and driverless vehicles are becoming the new norm.

So how does a brand that celebrates the visceral joy of driving stay relevant in an era of AI and autonomy? And what can other businesses—especially those outside the traditional tech space—learn from Hagerty’s approach to transformation and loyalty?

Tune in to find out, and don’t forget to share your thoughts: how do you balance tradition with innovation in your business?