What does it take to keep a brand built on classic car culture relevant in a world of automation, electrification, and AI? In this special episode of Conversations from the Show Floor, recorded live at the X4 Summit in Salt Lake City, we explore the answer with Maggie Stafford, Vice President of People Insights at Hagerty.

Best known for insuring collector cars, Hagerty has grown into something much more. Maggie explains how the company has evolved into a technology-enabled, community-powered lifestyle brand that serves more than 850,000 members worldwide. From grassroots meetups to high-profile events like Amelia Island Concours, Hagerty is creating space for car lovers to connect both on the road and online.

In our conversation, we unpack how a $20 million investment in cloud infrastructure is helping Hagerty meet modern expectations without losing sight of its core mission. Maggie shares how hands-on programs like “Stick Shift 101” and employee drives in vintage cars shape a culture that mirrors its customers’ passion. The goal is not just about providing coverage, but about keeping the joy of driving alive for future generations.

We also explore how Hagerty is navigating the shift toward digital service while maintaining personal connections. Maggie reveals how her small insights team is using feedback loops, data platforms, and smart tools to amplify member voices across the business. For brands wondering how to blend tradition with transformation, Hagerty offers a compelling example.

This episode touches on culture, technology, loyalty, and the art of scaling without losing identity. It’s a story of how one company continues to celebrate the analog joys of driving while embracing the digital realities of today.

Can nostalgia survive the next wave of innovation? Hagerty seems to think so—and they’re putting people, passion, and performance behind that belief.