Toronto-based Tailscale is on the cusp of surpassing 40,000 paid business clients—twice the number the secure networking technology startup had in November.
Avery Pennarun, Tailscale’s co-founder and CEO, attributes the company’s accelerating growth to its virality and rising AI demand, including among AI agents, which he said began heavily recommending, buying, and deploying Tailscale earlier this year.
Avery Pennarun, Tailscale
“Given the interest in Tailscale right now and the AI revolution in progress, doing a bit of a land grab is worth it.”
“Tailscale is, almost by accident, the tool of choice for a lot of AIs and AI agents that are running around now,” Pennarun told BetaKit in an exclusive interview.
Tailscale, which was recently featured in BetaKit Most Ambitious, sells low-configuration virtual private network (VPN) software to companies. The now 300-person firm’s clients include Cohere, Duolingo, Instacart, Lovable, Microsoft, Mistral, Nvidia, SAP, and Telus.
Tailscale announced its latest customer milestone on Tuesday alongside the appointment of Mike Shaver as vice-president of engineering. Shaver, who previously served in engineering leadership roles at Facebook, Fastly, and Mozilla, and worked as a distinguished engineer with Shopify, has been tasked with guiding Tailscale through the next phase of its scaling journey.
This will involve ensuring Tailscale’s platform is as frictionless as possible for both the AI agents and the humans using them, while maintaining its performance and security as it grows and more applications are developed on top of it. Shaver’s experience helping Facebook and Mozilla navigate similar stages is what attracted Pennarun.
Tailscale’s OpenClaw moment
As pressure to adopt AI has created a “Wild West” for corporate cybersecurity, Tailscale has been working to build a kind of air traffic control for AI agents through Aperture.
Pennarun said the release of OpenClaw, a highly autonomous open-source AI agent that quickly soared to millions of active users, was a “magical inflection point.” He thought the associated spike in popularity Tailscale saw on the back of surging OpenClaw demand would be short-lived and followed by high churn. But thus far, those customers have been sticking around, which he attributed to a combination of “incredibly good luck” and the strength of Tailscale’s product.
“It’s rare that you see that kind of new source of signups with such a high retention rate, straight out of the gate,” Pennarun said.
According to Tailscale’s customer onboarding survey, most of the firms it has added over the past eight months are using the startup’s software as part of their AI infrastructure stack.
Pennarun is also heartened by upstream numbers Tailscale has posted during this time, pointing at the 100 percent year-over-year growth the company has seen in both private Tailscale network creation and retention. It also now has two million monthly active users.
“As exciting as our growth rate is right now, I feel like we’re getting started,” Shaver told BetaKit in an interview, noting that Tailscale today reminds him of his early Firefox days.
The next level
Shaver has been a Tailscale fan for a long time. “The stage of growth that they’re in right now is one where my experience can be very valuable,” he said. “I have grown a number of organizations from this point to that next level, including Firefox and the Facebook mobile app.”
He replaces former VP of engineering Andrew Mitchell, whom Pennarun said recently stepped down to pursue other earlier-stage opportunities after two years putting the company “into a really good position.” BetaKit has reached out to Mitchell for comment.
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Pennarun did not share Tailscale’s revenue but claimed it is on track to double its sales in 2026, something it has done every year since launching in 2019.
The CEO said Tailscale, which closed a $230-million CAD Series C round at a $2-billion valuation last year, remains well-capitalized and could become profitable in under a year with its existing balance sheet. But with “a lot of wind blowing at [the company’s] back,” Pennarun said Tailscale is weighing the possibility of raising additional funding in the near future to grow even faster.
“Given the interest in Tailscale right now and the AI revolution in progress, doing a bit of a land grab is worth it,” Pennarun said.
Feature image courtesy Tailscale.