Saying 'Yes' More and Scaling the Future of Hagerty Insurance | A Conversation with Jeff Briglia

A Conversation with Jeff Briglia, President of Insurance at Hagerty

Listen to the full episode on Apple or Spotify.

Key Takeaways for Agents

• Hagerty’s advantage is focus | Deep understanding of the enthusiast mindset drives better products, claims outcomes, and service experiences.
• The future is about saying yes more | Hagerty is investing in broader eligibility, fewer underwriting blocks, and a faster, simpler agent experience.
• Agents remain central to growth | Hagerty sees agents as trusted advisors protecting high-value households and is building tools and processes to help them win more business with confidence.

Jeff Briglia serves as Hagerty’s President of Insurance, leading all aspects of insurance operations across direct-to-consumer and B2B channels, partnerships, claims, service, and product development.

In a recent episode of The Accelerator podcast, Jeff sat down with the hosts for a candid conversation about his career path, what drew him to Hagerty, and where he sees the future of Hagerty Insurance heading – especially for agents and brokers.

What follows is an edited Q&A from that conversation, shared in Jeff’s own words.

“I Had No Idea What Insurance Even Was”

Q: Jeff, how did you get into insurance?

Jeff Briglia: “It’s a funny story… I had no idea what insurance even was. I was good at math, went to school to be an engineer, worked as an environmental engineer, and then went back to get an MBA.”

After business school, Jeff moved into management consulting—but the nonstop travel conflicted with his priorities as a new parent.

“I wanted something more stable. I literally applied to Progressive for a product manager role as a practice interview. Once I started talking with them, I realized how interesting the business was. You’re selling something without fully knowing the cost yet—that’s fascinating.”

That practice interview turned into a job offer—and a 20+ year career in insurance.

“My practice interview ended up turning into a job offer and I was completely sold.”

Culture, Curiosity, and Career “Zigzags”

Q: What kept you in insurance—and shaped how you lead today?

Jeff: “At Progressive, the culture was incredible. Smart people, focused on winning, with a lot of autonomy. I was able to make an impact.”

Jeff’s career didn’t follow a straight line. Instead, he moved across product, customer experience, finance, claims, call centers, and general management—driven by curiosity.

“I came to believe that the more one area understands another area, the better decisions we make. That cross-functional understanding builds trust and helps organizations move faster.”

That belief now informs how he leads at Hagerty.

Why Hagerty Felt Different

Q: What made you say yes to Hagerty?

Jeff: “From the very first conversation, I was impressed by the ambition of the company and the leadership perspective.”

But what stood out most was clarity.

“Hagerty has a very clear definition of who its customer is. Many insurers serve ‘anyone who drives a car.’ That makes it hard to really know your customer.”

At Hagerty, that isn’t the case.

“They know the cars. They know the mindset. They’ve spent decades building solutions around that enthusiast lifestyle.”

“It feels like I’ve discovered a secret level in the insurance video game - and that level is Hagerty.”

How Customer Understanding Shows Up in Claims, Service, and Product

Q: How does that deep understanding translate into insurance experiences?

Jeff: “Let me start with claims—because that’s the moment of truth.”

Classic and collector vehicles are uniquely difficult to repair, and Hagerty has invested heavily to support that reality.

“We’ve invested millions of dollars building an ecosystem of claims experts, specialty shops, and parts knowledge. That’s how we get these cars back on the road where they belong.”

Service follows the same philosophy.

“Our teams are trained not just on policies, but on the hobby itself. We’ve even had employees restore cars so they understand what that process is really like.”

And product design reflects emotional value, not just replacement cost.

“Coverage like track-day protection or Cherished Salvage® exists because these cars matter deeply to their owners.”

Looking Ahead: Growth, Modernization, and “Saying Yes More”

Q: What excites you most about the next few years?

Jeff: “Our market is big, and demand is strong. We’ve always been a fast-growing company, and I expect that to continue.”

But Jeff is clear that growth isn’t just about volume—it’s about experience.

“I want the customer experience and the agent experience to be even better—simpler, faster, more modern. Insurance is complicated, but the experience doesn’t have to be.”

A core theme going forward:

“I just want to be able to say yes more.”

That means expanding eligibility and reducing friction.

“There are enthusiasts who love their cars and care for them, but don’t fit perfectly into our traditional guidelines. We’re looking at how to serve more of those customers - either by evolving underwriting or building new solutions.”

The Next Generation of Enthusiasts

Q: Are younger generations as passionate about cars?

Jeff: “Absolutely. The psychology is the same—the cars are just different.”

Instead of a ’57 Chevy, it might be a Miata or a newer Porsche - but the emotional attachment is just as strong.

“We have to evolve as a business to serve those customers just as well.”

Agents and Brokers: Central to the Growth Story

Q: How do you view the role of agents in Hagerty’s future?

Jeff: “Being an independent agent is hard. I have deep appreciation for the challenges.”

Hagerty’s role, Jeff says, is to protect the agent’s most important relationships.

“These are high-value households. When a claim happens, agents need confidence that their client will be taken care of.”

Guaranteed value coverage is a key differentiator.

“With daily driver policies, you often get actual cash value. With Hagerty, that agreed value matters - especially when the car is emotionally significant.”

Jeff also emphasized investments underway to improve the agent experience.

“We’re reducing underwriting blocks, making things faster, simpler, and easier. I don’t want agents quoting a policy only to hit unnecessary friction. I want to say yes more.”

Ending the Year on the Right Note

To close the conversation, Jeff shared a piece of advice that reflects both his leadership style and Hagerty’s purpose-driven culture.

“Try to end each day better than it began. Be a force for good.”

Want to Go Deeper?

Listen to the full episode of The Accelerator featuring Jeff Briglia to hear the complete conversation - including leadership lessons, agent insights, and the story behind Jeff’s newly acquired 1966 Sunbeam Tiger.

Explore more resources, episodes, and tools for agents at hagertyagent.com.