Robert Cassell

About Robert Cassell

I’m a product executive who has spent more than 16 years at Hagerty, growing alongside the company as my scope and responsibilities expanded across product strategy, platforms, and partner ecosystems. My work has centered on building strong product organizations—aligning vision, teams, and operating models to deliver outcomes that matter for both customers and the business.At Hagerty, I’ve led enterprise product portfolios spanning digital commerce, core insurance platforms, and large-scale partnerships. I’ve helped guide the organization from project-based delivery to a product-centric approach, established product and technology KPIs to support better decision-making, and built teams capable of operating at scale. Most recently, I’ve served as the executive lead for Hagerty’s strategic partnership with State Farm, guiding product and platform alignment across one of the most complex integrations the company has undertaken.Outside of work, I’m grounded in family and the outdoors. Long before my career in automotive and insurance, time spent outside and in outdoor-focused businesses shaped how I think about sustainability, craftsmanship, and long-term value. Those influences carry into my leadership style today—practical, thoughtful, and focused on building things that last.I believe great product organizations are built on clarity, trust, and accountability. As a leader, my role is to set direction, develop people, and create the conditions for teams to do their best work. I’m especially interested in conversations around human-centered design, thoughtful leadership, and the role time spent in nature plays in shaping how we think, create, and connect.

Experience

1. Vice President, Insurance Business Partnerships & Partner Programs

   Hagerty

   May 2022 — Present · US

   Executive lead for Hagerty’s strategic partnership with State Farm, representing the most complex partner integration in the company’s history• Owned end-to-end alignment across product, platform, technology, and operations to ensure partner capabilities and customer experiences were integrated into the broader product ecosystem• Led cross-functional leadership teams to establish governance, prioritization, and execution models that balanced speed, risk, and long-term scalability• Partnered with executive leadership to align partnership strategy with Hagerty’s long-term product vision, platform roadmap, and growth objectives•

Education

• Central Michigan University

  Bachelor of Science (BS), Remote Sensing GIS & Cartography, Environmental Studies, Land Use Planning

  1997 — 2001