The Toronto-based cybersecurity firm is committing millions of dollars over several years to develop versions of its networking software that customers can fully control and run on their own computing infrastructure. Patricia Prewitt, formerly a general manager at Google X’s Moonshot Factory, will lead the project. Tailscale plans to hire at least 50 people for the initiative, concentrating hiring in Toronto, Ottawa and Vancouver. (The Logic, Bloomberg)

Talking point: Tailscale’s technology connects companies’ devices so their computers and software can communicate securely. Its clients include Cohere, Microsoft, Duolingo and Instacart. The firm has raised over US$277 million to date, with a valuation of US$1.45 billion as of April 2025, according to PitchBook, and has reportedly doubled its roster of business customers to 40,000 since November 2025. CEO Avery Pennarun said being Canadian has been a big advantage lately, with more customers, particularly in Canada and Europe, concerned about security implications of using American AI. “You start going into Europe and they’re like, ‘I will buy anything, but not American technology,’” Pennarun told Bloomberg.

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