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Joshua Pillsbury

Co-founder & Managing Partner, Summit Commercial Solutions

Insurance

Joshua Pillsbury is co-founder and managing partner of Summit Commercial Solutions, a Kelowna commercial insurance brokerage that places business insurance for Canadian companies and builds software for its own brokers rather than replacing them. He started Summit in 2022 with Davis Gilbert; both had worked at Apollo Insurance. Summit's site calls him an underwriter turned insurtech founder.

Joshua hasn’t spoken on a TechTO, TechVancouver or TechWaterloo stage. This profile is here because Joshua co-founded Summit Commercial Solutions.

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Quick answers

Did Joshua Pillsbury co-found Summit Commercial Solutions?

Yes. Summit's own About page, checked on 2026-10-16, lists Joshua Pillsbury as Co-Founder & Managing Partner and says the company was founded in 2022. Coverager (2025-12-02) says Summit was founded in 2022 by former Apollo Insurance employees Davis Gilbert and Josh Pillsbury. Reinsurance News (2025-12-08) says it was launched in 2022 by the same two, and Insurance Business Canada (2024-04-15) calls them Summit's co-founders and managing partners.

What did Joshua Pillsbury do before Summit?

Summit's About page, checked on 2026-10-16, describes him as an underwriter turned insurtech founder and an operations leader with a background in scaling tech-enabled services. Coverager (2025-12-02) says he and Gilbert are former Apollo Insurance employees. No fetched page gives his title at Apollo or the dates he worked there.

Has Joshua Pillsbury spoken at TechTO?

No, and neither has co-founder Davis Gilbert; Summit has no TechTO stage appearance. Kieran Knock, who now leads revenue operations at Summit, spoke at TechTO in 2021 while a team lead at APOLLO Insurance.

Where is Joshua Pillsbury based, and what is he doing now?

Summit's About page, checked on 2026-10-16, still lists him as Co-Founder & Managing Partner. No fetched page states where he lives. He has been quoted on both of Summit's raises: on the $3.5 million seed round led by IA Capital Group, he told Insurance Business Canada (2024-04-15) the money would go to scaling day-to-day operations, hiring producers and bespoke technology; on the $7.5 million Series A led by IA Capital with Sorathia Holdings and Greenlight Re Innovations, Coverager (2025-12-02) quotes him saying the investment accelerates Summit's ability to scale nationally.

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Maintained by TechTO · facts sourced and dated · last reviewed Oct 16, 2026