Elevating the digital experience for car enthusiasts

The Opportunity

Hagerty had evolved far beyond a traditional insurance provider, becoming a lifestyle brand deeply embedded in automotive culture through events, media, memberships, marketplaces, and enthusiast communities. The challenge was to create a digital experience that reflected this broader ecosystem while modernizing how users interacted with the brand online.

The existing experience needed to better communicate Hagerty’s unique position within the collector and enthusiast automotive space while supporting a growing range of products, services, and community-driven offerings. The goal was to create a more emotionally engaging and premium digital experience that appealed to both longtime collectors and a new generation of automotive enthusiasts.

My Role

As Design Director, I helped to lead the experience and visual design direction for the initiative, helping define how the Hagerty brand translated into a modern digital ecosystem.

I collaborated with cross-functional teams across strategy, product, content, and engineering to shape the overall user experience, information architecture, and visual framework. My role focused on balancing premium editorial storytelling with usability, scalability, and commerce-driven functionality across the platform.

Approach

The experience was designed to feel less like a transactional insurance website and more like a destination for automotive culture.

A major focus was creating a richer content and storytelling ecosystem that unified insurance offerings, enthusiast resources, editorial content, memberships, and community experiences into a cohesive platform. The design direction embraced elevated typography, immersive automotive photography, cinematic layouts, and modern interaction patterns that reflected the emotional connection enthusiasts have with their vehicles.

Key areas of focus included:

• Repositioning the digital experience around automotive lifestyle and community

• Simplifying navigation across a growing ecosystem of services and content

• Creating scalable UI systems for editorial, marketplace, and membership experiences

• Elevating the premium feel of the brand through visual storytelling and motion

• Improving responsiveness and accessibility across devices

• Designing flexible frameworks capable of supporting future platform growth

The experience balanced emotional brand expression with practical usability, ensuring users could seamlessly move between content discovery, membership engagement, and service-related tasks.

Outcome

The final experience helped reposition Hagerty as a modern automotive lifestyle brand rather than solely a traditional insurance company, creating a more unified and premium digital ecosystem across content, community, memberships, and services.

Shortly after the launch of the redesigned experience, Hagerty successfully went public on the New York Stock Exchange — marking a major milestone in the company’s evolution and growth trajectory. While the IPO was the result of many contributing business factors, the work helped support a broader transformation effort by modernizing the brand’s digital presence, elevating customer perception, and creating a scalable platform aligned with Hagerty’s future-facing vision.

The project demonstrated how strategic experience design can play a meaningful role in helping legacy brands evolve, expand their audience, and strengthen market confidence during periods of major organizational growth.

Credits

Design Director: Nick Boes
Design Director: Jimmy Walker
Principal Designer: Tony Yoo
Sr. Product Designer: Josh Martens
Sr. Product Designer: Nicholas Swardt
Product Designer: Caitlin Sowers
Product Designer: Erik Maxwell
Product Designer: Veronica Benduski
Product Designer: Iesha Smith
UX Designer: Eva Kang
Lead Engineer: Mat Blyszcz