Avery Pennarun
Background
Avery Pennarun is a Canadian computer scientist and entrepreneur. He previously co-founded Netopia, authored popular open-source software (such as bup and sshuttle), and spent five years at Google leading networking, Wi-Fi hardware, and software platforms for Google Fiber.
Role at Tailscale
Avery Pennarun is the co-founder and Chief Executive Officer of Tailscale. A legendary systems thinker and technology essayist whose writings on software architecture are widely read across the tech industry, Pennarun recognized that corporate networking was fundamentally broken by hub-and-spoke hardware legacy thinking.
Under Pennarun's pragmatic leadership, Tailscale built a beloved brand with near-zero marketing spend, scaled from seed stage to a $1.0 billion unicorn, and created a remote-first engineering culture celebrated for technical excellence, empathy, and intellectual clarity.