MADISON, Wis., Sept. 24, 2025 /PRNewswire/ -- 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 recent investment and strengthens that commitment. Her experience driving claims innovation at scale will help us push the industry forward and deliver even greater value to carriers, contractors, and policyholders."

Olson's decision to join RoofMarketplace reflects her confidence in the company's vision. "The claims industry has been waiting for solutions that deliver real results without adding complexity," said Gwen Olson. "RoofMarketplace is that solution for roof claims, and I'm excited to help scale its impact across the insurance ecosystem."

The RoofMarketplace platform gathers up to three market-accurate bids for roof claims within 24–48 hours, reducing cycle times and ensuring fair, accurate settlements. By connecting carriers, vetted contractors, and homeowners in a transparent workflow, the company streamlines claims fulfillment, provides contractors access to qualified opportunities, and homeowners gain confidence in the repair process. Moreover, the platform offers support to every party involved, ensuring no one is left navigating the claims process alone or stuck in the middle without clarity or guidance.

Olson joins RoofMarketplace on the heels of a strategic growth investment and a wave of new leadership aimed at accelerating claims innovation. With fresh capital and a strengthened executive team, RoofMarketplace is positioned to scale its impact and continue transforming the roof claims process for carriers, contractors, and policyholders alike.

About RoofMarketplace

RoofMarketplace is a trusted marketplace reinventing the roofing claims experience. Homeowners, insurance carriers, adjusters, and local, vetted contractors connect through our platform to ensure top-quality, warrantied roofs are repaired or replaced at competitive prices—without the hassle. For more information, visit www.roofmarketplace.com or contact info@roofmarketplace.com.

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SOURCE RoofMarketplace Inc.