After working for his father’s architectural firm, Brian Jessen became interested in the financial side of project management, including residential new construction and renovation projects. Though he originally intended to pursue investment banking, the financial market during the late 1980s changed those plans.

“I stayed in Chicago and joined a local bank in their rotational training program,” Jessen says. “That is when I gravitated toward private banking and eventually residential mortgage lending.” 

Now, with more than 30 years of industry experience, Jessen is a senior lender and senior vice president at Wintrust Mortgage Corporation. Known less as a salesperson and more as a trusted resource, he specializes in jumbo mortgage loans, residential construction and renovation projects, plus first-time homebuyers’ loans and portfolio lending.

“We are good listeners and problem-solvers, giving honest advice with a straightforward process and with a clear plan of action,” Jessen says.

In 2023, Jessen won the Illinois Mortgage Bankers Association’s award for Best Loan Originator in Illinois for a Community Bank. He is also a consecutive recipient of the Five-Star Professional Award and consistently receives a Net Promoter Score of 95%+ in client satisfaction ratings (the average rating is 60%).

Additionally, Jessen is an affiliate member of North Shore-Barrington Association of Realtors, a founding member of PowerHouse SMART and a member both of Network in Action and ProVisors.

Outside of work, Brian supports Soldiers to Sidelines, which trains and places former military personnel in high school and college coaching careers, as well as Cradles to Crayons, which provides inner-city youth with education resources.

Finalists

Gabriel Gomez, JPMorgan Chase
Sam Sharp, Guaranteed Rate