You ever try getting three roofers to agree on anything? That’s like herding cats during a hailstorm, with a clipboard and a claims adjuster. But that’s the grind the insurance industry signed up for. Billions bleeding out in roofing overpays, adjusters buried in boots-on-roof site visits, and homeowners caught in the middle of the world’s least sexy tug-of-war.
And then along came RoofMarketplace, a software-powered broker of peace deals between carriers, contractors, and customers. The team just locked in $7 million in Series A funding to do one thing better than anyone else: bring logic, transparency, and scale to one of the most analog corners of the $20B-a-year roofing claims market.
Wingra Capital led the round, with Nick Jackson and crew seeing what so many missed: a rare combination of audacity, traction, and receipts. Backed again by Rock River Capital Partners and InnovateHealth Ventures, this isn’t first-time money, it’s conviction capital from people who’ve seen the roof and know it doesn’t need more shingle.
Credit where it’s due. William Bazeley, Timothy Russell, and David Kish saw the mess in 2011. Not from a whiteboard, but from the trenches, watching insurance carriers bleed millions on guesswork estimates. So they built a platform that delivers three real contractor bids 95.7% of the time… using aerial imagery. No ladders. No lunch breaks. Just data, precision, and 24- to 48-hour turnarounds that make the old guard look like it’s using rotary phones.
Today, Scott Holewinski steps in as CEO with that rare Midwest-meets-cybersecurity operator energy, fresh off exits like Tetra Defense and Gillware. Backed by Brian Beermann as CTO and Lauren Reid leading comms, this isn’t a team finding its way. It’s a team choosing its next summit.
Over $3.5B in bids. $1.4B in claims settled. $60M+ in GTV driven to local roofers. And if you think that’s impressive, ask yourself why 94% of carriers using RoofMarketplace actually say so, publicly.
With storm season rearing its head and LAE reserves sitting on $149B in delays, this is no longer just a “roofing tech” story. This is infrastructure-grade digital transformation. Powered by contractors. Validated by carriers. Designed for a world where the roof isn’t the problem, it’s the opportunity.
