Avery Pennarun is the founder of Tailscale. Tailscale has raised $272M, latest Series C $160M (2025). Cybersecurity · Toronto, Ontario, Canada.
Avery Pennarun is the founder of Tailscale. Tailscale operates in Cybersecurity and is based in Toronto, Ontario, Canada. Tailscale has raised $272M, latest Series C $160M (2025). Backers on record include Arthur Patterson, Jeff Clavier, Tom Drummond, Accel, Heavybit, Uncork Capital.
This founder profile draws on disclosed rounds, filings and investor records in the StartupFundraising database and is updated as new funding is recorded. Founders raising now use profiles like this one to study comparable Cybersecurity journeys in Toronto — who backed them, at what stage, and how much they raised.
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