Kyle Gillespie believes the lenders who stand out in today’s market are the ones who combine technology, strategy and human guidance. With more than 20 years of experience and over $1.25 billion in closed loan volume, he has built his business around helping clients and real estate partners navigate changing market conditions with confidence.
As senior vice president of mortgage lending at OriginPoint, Gillespie leads a team known for strong pre-approvals, proactive communication and reliable execution from contract to closing. In a market where speed and certainty matter more than ever, he focuses on delivering a high-touch client experience supported by modern tools that help create faster approvals, smoother communication and efficient transactions.
“The mortgage business has changed dramatically over the last few years,” Gillespie says. “You have to stay ahead of technology and market shifts, but at the end of the day, it still comes back to relationships, trust and giving people honest advice.”
As affordability challenges and limited inventory continue shaping the market, Gillespie helps buyers structure smarter offers and understand financing strategies early in the process. In 2025, he continued to distinguish himself as a top-performing loan officer in his division and was again recognized as a Scotsman Guide Top Originator. A multiyear member of OriginPoint’s Chairman’s Circle and President’s Club, he is known for his accessibility, communication and hands-on approach. Real estate partners value his ability to anticipate issues early and help buyers compete confidently through strategic guidance and strong execution.
Gillespie lives in Chicago’s Lakeview neighborhood with his wife and two daughters. Outside of work, he enjoys coaching softball, spending time with family and staying active in the community.
Applicant subject to credit and underwriting approval. Restrictions apply. OriginPoint LLC; NMLS #2185899. For licensing information visit nmlsconsumeraccess.org. Equal Housing Lender.
