Married for 35 years and in the mortgage business for even longer, Jay Jacobson knows a thing or two about longevity. Even he and his assistant have worked together for two decades. For Jacobson, however, longevity doesn’t mean being stuck in his ways; it’s quite the opposite. Though he has been a member of the Wintrust Honors Circle since 2017, he completely rebuilt his business over the last five years and was rewarded with induction into the President’s Circle in 2023.

When considering the secret to his success, Jacobson is quick to point to the support of his team in providing white-glove service to his clients as well as the knowledge he has gained over the years, which he applies to finding mortgage solutions. Though he was originally drawn to a mortgage career by the independence it would offer him, he stayed because of how rewarding it felt to help others achieve their homeownership goals.

In addition to “organized,” and “extremely helpful,” clients describe Jacobson as a clear communicator, a quality he values above all else when it comes to client relationships. “The mortgage-lending industry is very confusing and intimidating for consumers,” he explains. “The better your ability to break it down into more consumer-friendly communications, the more comfortable and at ease clients are.”

Jacobson takes the time to get to know his clients so he can learn as much as possible about their plans and goals, and then he educates them on how to get there. He has many resources to draw from to assist clients and is especially grateful for his colleagues and team members, whom he can bounce ideas off of and learn from their shared experiences. Jacobson is also a member of the Fox Valley Association of Realtors and the Northern Illinois Homebuilders Association.

Later this year, Jacobson and his wife will celebrate their 35th wedding anniversary with a trip to Europe. He also enjoys spending time with his growing brood of grandchildren.