Since we last caught up with him in 2020, Brian Jessen has experienced some big changes—the most significant of which was his move to Wintrust Mortgage. Transitioning from Guaranteed Rate, Brian saw an opportunity to broaden the way he and his team could support clients. Now, at Wintrust, they’re more than mortgage lenders; they’re partners in their clients’ financial lives, ready to assist with everything from investment planning to commercial lending. 

“At a big bank, clients may feel like they’re just a number, and smaller companies may lack the resources to meet all their needs,” Brian explains. “We’ve found a balance where clients feel truly seen and supported.”

Being part of a mid-sized bank allows Brian’s team to provide solutions that larger institutions might overlook and smaller companies may not be able to offer. Recently, Brian worked with a client who had just sold his large condo and was uncertain whether to buy an existing home or build a new one, and he didn’t know where to start in that decision-making process or who to turn to for the proper guidance. So Brian brought his years of experience to his client’s aid: they spent a considerable amount of time together hashing through the details and weighing the pros and cons of each option. By the end, the clear and easy choice was to build a new home. The client appreciated the level of Brian’s expertise and service.

“We looked at options that would fit his timeline and financial goals,” Brian recalls. “It’s this kind of comprehensive support that defines our approach. We’re here to help with every major life event—from planning for a growing family, to managing an inheritance, to divorce, and more.”

When Brian first considered moving to a new company, his priority was to ensure his clients had the right products and services, and that his team was positioned for even greater success. “Many of us have worked together for over a decade,” Brian says of his team. “We know each other's strengths, and we communicate seamlessly, ensuring every client receives high-quality service.”

“Consistency is one of our biggest strengths,” he continues. “When clients reach out to us, especially those we've worked with multiple times, they don’t have to reintroduce themselves or recount their financial history. This familiarity allows us to provide personalized advice that goes beyond just quoting rates.”

Brian designs each client experience to ensure a smooth, honest process that strengthens not only their relationship but also the client’s relationship with their REALTOR®. Honesty and transparency are crucial to making that happen: keeping clients informed, setting realistic expectations, and following through on every detail.

“When someone refers a client to us, their reputation is on the line as much as ours is,” he says. “There’s a rush in our industry to make big promises about speed or an over-the-top experience,” he explains. “We’d rather be realistic about timelines and deliver on those promises.” This refreshing honesty has helped Brian build strong, trusting relationships with agents who know that they can count on him to support their clients with care.

“The best partners are those who listen, understand what you need to be successful, and bring ideas that elevate your business,” Brian says about his approach to partnership. “It’s not about selling or self-promotion; it’s about meaningful collaboration that benefits everyone involved.”

For Brian, every partnership is personal. He isn’t just aiming to complete a transaction; he wants his clients to walk away with a positive experience and a strong foundation for future decisions. Whether it’s a client closing on their first home or a REALTOR® referring a new buyer, he is there to celebrate the moment, often showing up at closings to shake hands and share in the excitement. “That’s my reward,” he adds, “seeing that happiness on their faces.”

Looking forward, Brian is planning for even greater change. His team is gearing up to expand their services for first-time homebuyers and Spanish-speaking clients, as well as offerings for niche markets—such as renovation and new-construction financing—while expanding their mortgage program for medical professionals. Brian is also launching his own podcast series. It will feature short, insightful, engaging episodes designed to educate both clients and REALTORS® on everything from market trends to specific loan programs.

Outside of his business, Brian’s personal life has also entered a new chapter. With his kids now grown and spread across different cities, their family time has taken on a new dynamic. His oldest daughter’s move to Washington, D.C., alongside her boyfriend, who recently took a job with the Washington Nationals baseball team, was a big change. To help his daughter get settled, Brian reached out to a REALTOR® friend and client who has connections in the area. It’s one of the perks of his business: using his network to help his family and clients, no matter where life takes them.

As Brian and his team continue to evolve to meet the needs of their clients and referral partners, they remain anchored in the principles that have always guided them: trust, transparency, and a genuine commitment to seeing people succeed.