Sixteen years as a Chicago-area real estate broker has taught Jason Finn a critical lesson: The loan officers who could communicate effectively with agents were rare. In 2022, after a career spent on the other side of the transaction, he obtained his mortgage license with a clear mission — to become the lender he’d always wished he had on speed dial.
Finn’s path to lending wound through consulting first. Fresh out of college with a business degree, he worked for PwC and IBM in financial services and pharmaceuticals — traveling constantly — before jumping to real estate in 2006 to get off the road. He spent 16 years as a top-producing Chicagoland broker before his data-and-analytics background pulled him toward origination. Now vice president of mortgage lending at Key Mortgage Services, he thrives on the complex loans other lenders sidestep, such as non-warrantable condos, self-employed borrowers, down-payment assistance, multiunit properties and investment loans.
Clients regularly describe closings as smooth and ahead of schedule. Having started from scratch in 2022, Finn wrote nearly 100 mortgages in 2025. His rapid ascent earned him Key Mortgage Services’ Founders Club and Trailblazer awards; Chicago Agent named him its Social Media Influencer of the Year in the lender category for 2024.
When he isn’t securing loans, Finn is deeply committed to his community and his family. He organizes fundraising events for Camp One Step by Children’s Oncology Services, which sends children with cancer to camp. A serious poker player, he is set to attend his 20th consecutive World Series of Poker this summer. Above all, he values the downtime he gets to spend with his wife and two teenage children — the family just recently returned from an unforgettable trip exploring Tokyo.
