Wolf&Grayson EditorialLong-term client loyalty doesn’t come from annual policy reviews and competitive quotes alone. The real challenge in insurance is earning trust from someone who’s worked with the same broker for two decades. Jason Gesser has built his approach around a straightforward idea: help people in every way you can, not just with their insurance. Gesser didn’t take a traditional path into insurance. Growing up in Hawaii and spending years coaching college football shaped how he thinks about relationships. “Understanding relationships, how you treat people, regardless of whether they can bring you positive feedback or positive results or not, I think is a general way I live life,” he says.
Building Trust Through Connections
A story from his coaching days illustrates how Gesser thinks about building connections. While working as a high school football coach, he met with a college coach who came through to visit. They sat together for two hours talking football strategy on a whiteboard. “Fast forward, gosh, four or five years, I get a call from him and he said, ‘Hey, I want to hire you as my passing game coordinator, my quarterbacks coach.’ And he did—without even a formal interview, because he had already put me through one during that whiteboard session.”
That same principle got him into insurance. A wealth manager introduced him to a CEO who needed help with a side business. He spent nearly two years bringing investors to the table and connecting the company with NFL and college football teams. “Because I was able to provide value for him in other areas, he saw that I could translate to this area,” Gesser explains. The CEO eventually brought him into insurance, despite having zero experience in the industry.
Gesser sees every client relationship as broader than the policy itself. “I want to partner with people that I love working with, that I want to be a part of their lives. I want to be a partner for them, not just in insurance, but in general.” That could mean connecting someone with a financial advisor, helping get tickets to a game for a client’s daughter’s birthday, or introducing them to an attorney in a specific field. “I love being able to be that guy that comes through for somebody and being known for that,” he says. “I think that just builds the relationship and the care for your client, and it’s more genuine than just, hey, let me take you out golfing and we’ll talk for a couple of hours.” He’s not interested in surface-level business relationships. The connections he builds go deeper.
Handling Long-Term Client Loyalty
The toughest challenge Gesser faces? Clients with decades-long relationships with their current broker. “We hear all the time, ‘I’ve been with my guy for 20 years. I’ve known him since high school. He’s my brother-in-law,'” he notes. While he respects that loyalty, there’s often a problem lurking underneath. These long-term relationships tend to run on autopilot. “That broker is on autopilot. He’s relying solely on his relationship, not really making the adjustments or looking at the business needs that are there for their coverages,” Gesser observes. The technical side gets neglected. Coverage structures don’t get updated. Contract language doesn’t get reviewed properly. “You also have to back it up with what you’re doing annually and making sure that the technical side, the carrier side, the relationship side with the underwriters, the safety programs, the contract reviews—all those things are dialed in each year.” Getting someone to even look at their existing program becomes the real battle. Gesser refuses to take shots at competitors to win business. “I’m never going to be a negative recruiter,” he states firmly. “Let us show you what we can do and the value we can add. And if you feel that’s significant enough and we can work together and create that partnership, then let’s work together.”
Embracing Patience in Partnerships
Patience defines his strategy. He’s known some clients for 20 years before they agreed to review their insurance programs. Even then, it took another two or three years of building trust. “It’s a long-term game, it’s not a short-term game,” he says. “Those are the clients and partnerships that you want.” This thinking extends to how he helps people outside of insurance work. Gesser looks for ways to add value everywhere. “Is your kid looking for a new coach? Do you need help, do you need any kind of attorney help in certain industries? Can I help you with a couple of tickets to the game so you can go and show her a great time?” Anything that helps make someone’s life easier or makes them look good strengthens the relationship. Eventually, that translates into a chance to earn their business. “My life as a commercial insurance broker,” Gesser explains, “is built around relationships, and it’s about bringing value to somebody’s life in so many different ways beyond just that. That’s just your lifestyle and you don’t even think about it any other way.”
He sees value in technology for handling administrative tasks and technical work. AI could help him stay on top of quarterly touchpoints with clients or draft quick emails when time is tight. “My time is so crunched and I’m looking at everything else to help keep those touchpoints on and keep that relationship going,” he says. The real benefit will come from technical efficiency. Reviewing policy language, scouring through contracts, and analyzing endorsements currently take hours. With AI, those tasks could happen in minutes. “Rather than taking us an hour or two hours to go through a policy agreement or language on endorsements or language on risk transfer, it will now take five minutes or less with AI.”
But he draws a hard line at replacing personal interaction. “I love having that personal touch. I’m an old-school guy. I love sending handwritten notes,” Gesser says. Having AI pretend to be him in conversations with clients? Not happening. “As soon as they would find out that was AI and not you, you’re in a world of hurt. They then start questioning you and you start losing some trust.”
Connect with Jason Gesser on LinkedIn to explore his relationship-first approach to insurance and client partnerships.
