Insurance has a reputation problem. Most business owners see it as something they have to deal with once a year, begrudgingly fill out paperwork, and hope for the best price. Jason Gesser thinks that’s backwards. As a VP at HUB International, he’s spent six years showing companies how insurance can actually work for them instead of against them.
Transforming Traditional Broker Practices
Gesser didn’t start in insurance. His career began in sports, first playing, then coaching, and later broadcasting. “I’ve used my history and background to transition into the business side of things,” he says. The teamwork, discipline, and relationship-building skills he honed on the field translated naturally when he entered commercial insurance six years ago. About six months ago, he joined HUB International, one of the country’s largest brokerages, where he brings a client-focused approach that stands apart from the industry norm. Too often, he argues, brokers act like “glorified mail carriers.” As he explains, “Traditionally, clients experience someone showing up with a stack of applications. You fill them out, the broker takes them to the market, and then comes back with whatever the market decided.” That process leaves clients feeling powerless over both costs and coverage. Gesser’s model flips the script by engaging clients proactively, giving them a voice in the process, and treating insurance as a strategic tool rather than an inevitability.
Explaining Insurance Pricing Clearly
Gesser’s strategy centers on transparency. He shows clients how insurance pricing really works and what levers they can pull to influence it. “You have to understand what their perspective is,” he notes. Most business owners have never seen how carriers evaluate risk or price policies. Gesser walks them through the process, explaining which factors drive costs and what changes can strengthen their risk profile. “This could be for tax purposes, risk mitigation in certain areas, or looking forward and investing money strategically,” he says. The market itself is also tightening, with fewer carriers willing to take on certain risks. “You have to become more attractive to these underwriters and carriers,” Gesser explains. His role is to present clients in the best possible light, whether they have a history of claims or a clean record.
At HUB International, scale provides another advantage. With data from thousands of companies across multiple markets, Gesser can spot patterns and benchmarks that a smaller broker might miss. “Insurance is big data. It’s all about what percentage of risk carriers are going to take on,” he says. Instead of treating each client in isolation, he can compare their profile to similar businesses and identify proven strategies. Technology accelerates that process. “Being able to have that big data and analyze those patterns is huge,” Gesser notes. AI adds another layer, helping clients evaluate options more quickly and understand which approaches are most likely to work for their situation.
Negotiating Policy Language for Savings
One area where Gesser stands out is policy language. Many brokers, he says, never push back on the fine print. “A lot of brokers don’t even realize that if you just push back on some of the language and policy coverages, you can get things added on for no cost at all, or for very minimal cost,” he explains. The impact can be enormous. Small adjustments or additional endorsements may save clients hundreds of thousands of dollars when a claim arises. It takes deep industry knowledge and the willingness to negotiate line by line. “A lot of brokers don’t want to take the time or energy to go through all those details,” Gesser admits. For him, that diligence is part of what sets a true advisor apart from a middleman.
Building Ongoing Risk Partnerships
Most brokers disappear after renewal and only reappear a year later. Gesser takes a different approach. “Success to me with a client is having quarterly reviews and being able to strategize together,” he says. He wants clients to see his team as risk management strategists, not just insurance vendors. That means getting involved in contract negotiations, business planning, and ongoing risk assessments. “Clients come to us with contract negotiations and questions: ‘What do you see here? What are the risks there?’” he explains. The goal is to become embedded in a client’s operations. “We are business partners. We’re part of their company. We’re part of helping them make their business better and protecting their operations.”
This partnership mindset also supports employee retention, a challenge many companies face today. Comprehensive risk management strategies help employees feel secure and valued, showing that their organization takes safety and wellbeing seriously. For Gesser, the shift business owners need to make is one of perspective. “View insurance as a tool,” he advises. “Once you learn how to look at insurance as a tool rather than just something that you have to do, that’s when your mindset shifts and you start understanding the true value of your insurance program.”
Connect with Jason Gesser on LinkedIn to explore smarter insurance strategies for your business.
