Setting the Stage
On September 11, the Hockey Hall of Fame in downtown Toronto transformed into more than a shrine to Canada’s game. It became the arena for the Guidewire Insurtech Vanguards InsurPitch Toronto 2025 competition, led by Guidewire’s Chief Evangelist, Laura Drabik. Laura launched Guidewire's insurtech incubator, the Insurtech Vanguards. The venue buzzed with energy as insurance leaders, innovators, and insurtech founders came together to see who would skate away with victory.
Music pulsed through the hall as attendees streamed in, creating an atmosphere that felt closer to a championship match than a corporate event. With the Stanley Cup gleaming nearby and the crowd buzzing with anticipation, the stage was set for a night of bold ideas, tough questions, and plenty of Canadian spirit.
The Lineup
This year, 13 insurtechs entered the competition, narrowed down by more than 3,000 online votes to five finalists: ProNavigator, Tempo, QuickFacts, Wisedocs, and Sky Tech AI.
The judging panel brought together six industry leaders including Catherine Desgagnés-Belzil, EVP & Leader of Business Performance and IT at Beneva, James Warburton, CIO at Gore Mutual, Imran Ilyas, Partner at PwC and sponsor of InsurPitch Toronto, Laviva Mazhar, Principal at Luge Capital, Will Murphy, VP of Technology Alliances at Guidewire, and Tony Cronin, Director of Product Management at Guidewire.
Together, they took their seats in the judges’ box, ready to challenge, question, and ultimately crown a winner.
In the stands, the strength of Canada’s insurance market was on full display with 26 insurers represented, from household names like Allstate, Aviva, Chubb, Desjardins, and Intact to regional leaders like Commonwell, Echelon, and La Segunda.
The Competition Heats Up
One by one, the startups took centre ice. Each had just minutes to make their case, answer rapid-fire questions from the judges, and show how their technology could change the game for insurers and customers alike.
The pitches were as diverse as they were ambitious:
- Tempo accelerates speed-to-market, enabling insurers to launch digital products faster and stay competitive.
- Sky Tech AI unlocks insights from unstructured data, helping insurers turn information overload into smarter decisions.
- Wisedocs streamlines medical record review, cutting time and complexity in claims so adjusters can reach fair outcomes faster.
- QuickFacts simplifies underwriting comparisons, giving brokers clear insights to advise clients with confidence.
- ProNavigator delivers instant, AI-powered knowledge access for insurers and brokers — a true game-changer where speed and accuracy matter.
The crowd leaned in, cheering on their favorites and nodding as innovative solutions were unveiled. It wasn’t just polite applause — there was genuine excitement in the air.
Insurer Voices from the Stands
The attending insurers weren’t shy about sharing their enthusiasm. A CIO from a Tier 1 carrier declared, “This is the best insurance event out there.” Another executive, a VP from a standard lines carrier thanked Guidewire for “representing the Canadian insurance market.”
Even Guidewire employees were swept up in the moment. As one new hire put it: “This is why I joined Guidewire — to be in the middle of it all.”
These soundbites weren’t just feel-good lines; they captured the momentum of an industry hungry for practical innovation.
A Hockey Legend Takes the Stage
Before the judges revealed their decision, the crowd was treated to a special guest: Mike “Kruzer” Krushelnyski, former NHL star and Stanley Cup champion.
From the rink to the stage, Kruzer brought the same grit, vision, and energy that defined his hockey career into the spotlight at InsurPitch. His message was simple but powerful: success in both sports and insurance innovation takes teamwork, resilience, and the courage to take bold shots. The audience roared with appreciation, the perfect prelude to the night’s big reveal.
And the Winner Is…
With the inspiration of a hockey legend still echoing in the room, the moment everyone was waiting for arrived. The judges conferred, the crowd leaned forward, and the announcement was delivered by Laura and Kruzer: ProNavigator was crowned the winner of InsurPitch Toronto 2025.
Cheers filled the Hockey Hall of Fame as ProNavigator’s team celebrated on stage, hoisting the metaphorical cup as the night’s champions.
Beyond the Pitches
Of course, InsurPitch wasn’t just about who took home the trophy. It was about connecting the dots between startups and insurers, sparking conversations in the networking breaks, and showing how innovation can thrive in a market as dynamic as Canada’s.
The vibe in the room reflected exactly that: people swapping business cards, debating the merits of AI versus human touch, and imagining how to bring these solutions to life inside their organizations.
And yes — there were raffles, laughs, and even some lucky winners walking away with signed hockey gear, courtesy of our generous hosts and sponsors.
Looking Ahead
With Toronto wrapped, the InsurPitch series isn’t slowing down.
Join Laura Drabik and her Insurtech Vanguards at future competitions:
- Las Vegas on October 15 at Topgolf during ITC.
- Pitch Off: Battle of the Best on October 28 at Guidewire Connections 2025.
The Canadian event proved once again that InsurPitch isn’t just a competition — it’s a movement. By bringing startups, insurers, and industry leaders together, we’re not just watching the future of insurance unfold. We’re building it.
Final Thoughts
Walking out of the Hockey Hall of Fame, you couldn’t help but feel the buzz. The conversations carried into the night, and the ideas pitched will no doubt echo through boardrooms and product roadmaps in the months to come.
InsurPitch Toronto 2025 wasn’t just about innovation on stage — it was about community, collaboration, and momentum. And with hockey legends like Kruzer adding to the mix, it’s safe to say this was a night to remember.