RoofMarketplace, a digital platform that connects insurers, contractors, and homeowners to simplify the roof claims process, has appointed Gwen Olson as Chief Strategy Officer. 

With more than 20 years of insurance leadership experience—including senior roles at American Family Insurance and Liberty Mutual—Olson brings expertise in claims digital transformation to guide RoofMarketplace’s next phase of growth and innovation.

"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.