GreenSky Ventures is proud to announce that one of its portfolio companies, ProNavigator, will be purchased by Guidewire Software Inc in a deal that was announced on October 28th, 2025.
Headquartered in Kitchener, Ontario, ProNavigator has built an insurance knowledge management platform that is used by leading insurance organizations. Guidewire is an American software company based in San Mateo, California, that provides property and casualty insurance solutions. Guidewire is a publicly traded company that is listed on the New York Stock Exchange (GWRE). More details can be found in the Guidewire press release here.
GreenSky has had a long relationship with ProNavigator: GreenSky Accelerator Fund II led the company’s first institutional funding round in 2018, and GreenSky Accelerator Fund III participated in the company’s second financing round in 2020. Several of GreenSky’s partners have been representatives on the board for the past seven years. GreenSky’s Greg Stewart said, “It has been a pleasure to work alongside the team. We believe that Guidewire is a perfect fit for ProNavigator, and we look forward to observing their continued growth.”
GreenSky extends our sincere congratulations to the entire ProNavigator team, and in particular, would like to acknowledge the accomplishments of CEO and Founder Joseph D’Souza.
About GreenSky Ventures:
GreenSky Ventures is a Toronto-based venture capital firm investing in early-stage Canadian technology startups. Through its affiliated GreenSky Accelerator Funds I–VI, the firm provides capital and strategic guidance to high-growth potential companies. Learn more at greensky.vc.
About ProNavigator:
ProNavigator is the AI-enabled knowledge management platform built for insurance. Their solution consolidates and delivers accurate, up-to-date answers for distribution, underwriting, claims, and customer service teams – so they spend less time searching and more time delivering value. With 34 insurance customers across the U.S. and Canada, ProNavigator is helping carriers, MGAs, and brokers work smarter, move faster, and serve better.
About Guidewire:
Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. More than 570 insurers in 43 countries, from new ventures to the largest and most complex in the world, rely on Guidewire products. With core systems leveraging data and analytics, digital, and artificial intelligence, Guidewire defines cloud platform excellence for P&C insurers.
