Tailscale
Leadership History
4 leaders · 2019 to present
Avery Pennarun is the CEO of Tailscale, in the role since 2019.
| Name | Role | From | To | Years in role |
|---|---|---|---|---|
| Mike Shaver | VP of Engineering | 2026 | Present | < 1 |
| Ross Kukulinski | VP of Product | 2026 | Present | < 1 |
| Avery Pennarun | Co-Founder & Chief Executive Officer | 2019 | Present | 7 |
| David Crawshaw | Co-Founder | 2019 | Present | 7 |
Tailscale makes private networking feel like logging into an app. Each device runs a Tailscale client that gets keys and access rules from Tailscale's coordination service and then builds encrypted WireGuard tunnels straight to the other devices it is allowed to reach. When firewalls block direct connections, traffic passes through Tailscale's DERP relays, which forward encrypted packets they cannot read. The company was founded in 2019 by Avery Pennarun, David Crawshaw and David Carney, who had worked together at Google on projects including Google Fiber. Brad Fitzpatrick, creator of LiveJournal and Memcached and a long-time Go team member, left Google and joined as a co-founder in January 2020. Tailscale launched publicly in 2020 and has been remote-first from the start, with Canadian roots in Toronto. Usage has grown fast. Tailscale passed 5,000 paying teams in early 2024 and reported more than 10,000 organizations using it in April 2025, including SAP and Hugging Face. By July 2026 it was nearing 40,000 paid business customers, with clients such as Cohere, Duolingo, Instacart, Microsoft, Mistral, Nvidia, SAP and Telus. The company is headquartered in Toronto, Canada.
VP of Engineering
2026 – Present
0 years (current)
Shaver managed the highly aggressive early product scaling, heavily pushing the absolutely critical 'zero-config' developer experience that caused Tailscale to go massively viral within enterprise engineering teams.
As an early executive and key operational leader, he helped translate deep, complex networking technology into an incredibly simple, highly commercial B2B product.
VP of Product
2026 – Present
0 years (current)
Kukulinski aggressively expanded Tailscale's integration with massive enterprise identity providers (like Okta and Azure AD), heavily driving the company's shift from a developer tool to a full Zero Trust enterprise platform.
As a senior product leader, he manages the absolute critical roadmap required to secure highly lucrative, multi-million dollar contracts with Fortune 500 CISOs.
Co-Founder & Chief Executive Officer
2019 – Present
7 years (current)
Kept Tailscale product-led with a large free tier, raised the April 2025 Series C from existing lead investor Accel without adding board seats, and in 2026 leaned into AI infrastructure demand with products such as Aperture.
Co-founded Tailscale and sets its product and company strategy.
Co-Founder
2019 – Present
7 years (current)
Crawshaw drove the absolute core technical thesis of building entirely on top of the open-source WireGuard protocol, strictly avoiding the massive complexity and unreliability of legacy IPSec VPNs.
As Co-Founder and CTO, he is the absolute visionary behind the platform's incredibly elegant, peer-to-peer routing architecture.
Tailscale competes with large security vendors that bundle zero-trust network access into broader platforms, including Cloudflare One, Zscaler Private Access, Palo Alto Networks Prisma Access and Cisco. It also faces open-source and self-hosted alternatives such as Headscale and NetBird, plus ZeroTier.
Rapid growth brings its own pressure. Customer counts roughly doubled between November 2025 and July 2026, much of it from AI teams and AI agents, so Tailscale has to scale support, reliability and security while keeping the product simple. The August 2026 Hugging Face intrusion, in which Tailscale said no vulnerability in its software was exploited, showed how often Tailscale now appears in AI infrastructure incident reports.
Avery Pennarun is the co-founder and CEO of Tailscale. A Canadian software engineer and entrepreneur, Pennarun graduated in computer engineering from the University of Waterloo and is renowned for creating foundational open-source tools including `sshuttle` and `git-subtree`, as well as co-founding NetCloth and WHAAM.
At Google, Pennarun served as a Senior Staff Software Engineer for over seven years, leading hardware and networking engineering for Google Fiber, building carrier-grade Wi-Fi routers, embedded Linux network stacks, and mesh telecommunications infrastructure.
In 2010, Pennarun created `sshuttle`, a popular open-source tool that acted as a transparent proxy server over an SSH connection, bypassing firewalls without requiring root access. The lessons learned about network routing, NAT, and proxy bottlenecks directly influenced Tailscale's mesh architecture.
Pennarun is widely admired across the software industry for his influential technical blog (apenwarr.ca). Essays such as "An Epic Trip Down the Memory Lane of Software," "How to write a fast web app," and "Cowboy Programming" are considered essential reading for systems programmers.
Pennarun structured Tailscale as a 100% remote-first company from its inception in 2019, long before the pandemic. He emphasizes asynchronous communication, written documentation, high employee autonomy, and eliminating unproductive status meetings in favor of tangible code output.
Pennarun authored definitive, accessible deep dives into complex networking protocols, notably "How NAT Traversal Works" (2020) and "How Tailscale Works." His clear explanations demystified STUN, ICE, and WireGuard, turning technical transparency into Tailscale's primary marketing engine.
Pennarun orchestrated Tailscale's capital rounds, raising early funding from Uncork Capital and Heavybit, securing a $17M Series A with Accel in 2020, and closing a landmark $110M Series B at a $1B+ valuation led by CRV and Insight Partners in May 2022.
Pennarun advocates for software that "just works" with zero superfluous configuration. He insists that Tailscale should operate silently in the background, handling complex mathematical routing and cryptographic handshakes without forcing users to understand networking internals.
Pennarun famously argues that "if security software is hard to use, people will bypass it." By making WireGuard encryption easier to set up than an insecure open connection, Tailscale ensures that the most secure path is also the path of least resistance.
Pennarun has been celebrated as one of Canada's premier technology founders, keynoting major open-source and cybersecurity conferences and earning accolades from the developer community for elevating developer experience (DX) in networking.
Pennarun fosters an empathetic, low-ego engineering culture where code commits, RFC discussions, and respectful peer reviews take precedence over corporate politics, attracting world-class systems programmers from across North America and Europe.
Pennarun aims to make traditional network security appliances obsolete, building an invisible, global zero-trust layer that seamlessly connects all devices, containers, and applications across the internet as if they were on a single secure local network.
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