Toronto-based secure networking startup Tailscale is closing in on 40,000 paid business customers, driven by rising demand from AI infrastructure and the widespread adoption of its VPN technology by AI agents.
- Customer base nearly doubles to 40,000 paid businesses since late 2025
- AI agents increasingly recommend and deploy Tailscale software
- New VP engineering Mike Shaver to guide next scaling phase
What happened
Tailscale, a Toronto-based startup offering low-configuration virtual private network software, announced it is nearing 40,000 paying business customers, a figure that has doubled since November 2025. The company’s growth is sparked largely by demand from AI infrastructure, as AI agents have started recommending and using Tailscale extensively since early 2026. This has led to steady retention and expansion despite initial expectations of potential churn.
Alongside this growth milestone, Tailscale appointed Mike Shaver as vice-president of engineering. Shaver brings tenures from Facebook, Mozilla, and Shopify, and his role focuses on scaling the company’s platform to handle increasing adoption while balancing performance and security. This leadership move follows the departure of the previous VP of engineering after two years of foundational work.
Why it matters
Tailscale’s growth trajectory is notable as it rides the wave of the ongoing AI revolution, where secure networking infrastructure is critical for managing AI agents and applications. The company’s software has become a key component within many AI infrastructure stacks, underscoring the rising importance of seamless and secure connectivity solutions in the AI-driven business environment.
The startup’s ability to retain customers acquired through AI-driven demand signals a durable product-market fit, while its solid financial footing after a $230 million CAD Series C round and rapid revenue growth positions it for potential profitability within the next year. This momentum could position Tailscale as a critical infrastructure player in the evolving cybersecurity and AI landscape.
What to watch next
The industry will be watching how Tailscale manages its scaling challenges under new leadership, particularly maintaining both high performance and strict security as its platform usage increases. Attention will also focus on how the company navigates the “Wild West” of AI-related cybersecurity demands, including its Aperture product aimed at controlling AI agents securely.
Additionally, market observers will be interested in any decisions Tailscale makes regarding additional funding, as the CEO indicated the company is considering raising new capital despite strong current financial reserves. Continued customer growth, product development, and sustained AI ecosystem integration will be key indicators of Tailscale’s next phase of success.