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Brian R. Jessen, Senior Vice President, Senior Lender

Wintrust Mortgage Corporation

After working for his father’s architectural firm during high school, college and shortly after receiving his finance degree, Brian Jessen became interested in the financial side of projects, including residential new construction and renovation projects. “Seeing how excited people were for their new dream home, which is when I gravitated toward private banking and residential mortgage lending,” he says.

In the industry for 32 years, Jessen is a senior vice president and senior lender at Wintrust Mortgage Corporation, which he describes as a company with a national reach but a local, very friendly feel.

Known as a trusted resource, he specializes in jumbo mortgage loans for primary and second homes, residential construction and renovation projects, first-time homebuyers, mortgages to medical professionals and portfolio lending. With a solid team of experienced sales assistants and processing staff members to support him, Jessen is business-driven but balances his lofty expectations with caring, kindness and gratitude. “My team and I provide honest advice and counsel,” he insists. “We are good listeners and problem-solvers, with a straightforward process and a specific plan of action. We will always do whatever is best for the client, which can mean sometimes that not getting a mortgage or borrowing against other assets is actually better for the client.”

Recognized for his excellence in the industry, Jessen has been a recipient of the Five Star Professional Award for over a decade. He was also voted 2023 Mortgage Loan Officer of the Year by Chicago Agent Magazine and the Illinois Mortgage Bankers Association. With a client satisfaction score (NPS) of 98%, well above the industry average of 60%, Jessen’s competence is unquestionable. He is an affiliate member of the North Shore-Barrington Association of Realtors (NSBAR), a founding member of PowerHouse SMART and a member of Network in Action (NIA) and ProVisors.

His charitable focus is on two entities: Soldiers to Sidelines, a program that trains and places former military personnel into high school and college coaching careers, and Gigi’s Playhouse, which provides no-cost support to children and adults with Down’s Syndrome.

Jessen is proud of getting his children through college and their master’s programs without incurring school debt. He enjoys volunteering, golfing, biking, and reading books and stories about interesting people giving back to their communities.

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