Avery Pennarun

Avery Pennarun

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Avery Pennarun is the co-founder and CEO of Tailscale, a Toronto-based virtual private network technology company. With a background in software engineering from Google, Pennarun has played a pivotal role in Tailscale's rapid growth, especially among AI companies, as the firm recently raised $230 million, reaching a valuation of $2 billion. Under his leadership, Tailscale has emerged as a preferred choice for businesses seeking efficient and secure networking solutions, capitalizing on the demand for direct, cost-effective connections in an increasingly digital workforce.

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Recent news mentions

Avery Pennarun is the CEO and co-founder of Tailscale, a rapidly growing tech company.

Tailscale, already one of Canada’s fastest growing tech companies, is gaining speed
The Globe and Mail·CanadaCanada· 2025-11-28
9.0

Avery Pennarun is the CEO and co-founder of Tailscale, which has rapidly become a leading virtual private network technology provider.

Tailscale raises $230-million, reaching $2-billion valuation on surging demand from AI companies
The Globe and Mail·CanadaCanada· 2025-04-08
9.0