RoofMarketplace Appoints Gwen Olson as Chief Strategy Officer to Accelerate Next Phase of Growth
Madison, Wisconsin – [September 24, 2025] — RoofMarketplace, the trusted platform transforming the roofing claims experience, today announced the appointment of Gwen Olson as Chief Strategy Officer. Olson brings more than two decades of insurance leadership experience, including deep expertise in claims digital transformation, to help drive the company’s next phase of growth and innovation. Olson joins RoofMarketplace after serving in senior roles at American Family Insurance, where she led initiatives to streamline claims operations and enhance customer experience. Prior to that, she spent over a decade at Liberty Mutual Insurance with leadership positions in claims technology and process modernization. Her ability to deliver scalable, tech-enabled solutions underscores why she is the ideal addition to help drive RoofMarketplace’s mission of modernizing property claims. “RoofMarketplace was designed to make roof claims faster, fairer, and easier for everyone involved,” said Scott Holewinski, CEO of RoofMarketplace. “Bringing Gwen on board builds on our
