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Avery Pennarun

Co-Founder & CEO, Tailscale Inc. · Canada

✓ Verified current role· as of 2026-09-11

Avery Pennarun is the CEO of Tailscale Inc.. Pennarun is based in Canada. Pennarun was educated at University of Waterloo.

Co-founder and CEO of Tailscale, a peer-to-peer VPN and mesh networking company. Previously led Google Fiber's gigabit WiFi and platform analytics team, and founded Net Integration Technologies (sold to IBM in 2008). Known for open-source projects including sshuttle, wvdial, and bup.

Recent developments

AI summary of recent coverage

Recent coverage of Avery Pennarun has focused on Tailscale's expansion strategy amid growing demand from AI adoption, including the company's exploration of mergers and acquisitions and the launch of identity-linked governance tools designed for AI agents and tools. Headlines also reflect the startup's rapid growth trajectory, including its $230 million CAD Series C funding round that valued the company at $2 billion, and discussions of a potential future initial public offering.

Summarized from the headlines below; see each source for the full story.

Citizenship
Canada
Education
University of Waterloo

Our coverage

On CEOInsider

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Avery Pennarun: FAQ

Who is Avery Pennarun?
Avery Pennarun is the Co-Founder & CEO of Tailscale Inc., based in Canada.
What company does Avery Pennarun lead?
Avery Pennarun is CEO of Tailscale Inc..
Where was Avery Pennarun educated?
Avery Pennarun studied at University of Waterloo.