Tailscale
Remote-first secure-networking company: a zero-config mesh VPN built on WireGuard (zero-trust access). Founded 2019, HQ Toronto. ~177 staff. $275M raised, $1.5B valuation (Series C led by Accel).
What is Tailscale?
Tailscale is a secure-networking company whose product is a zero-config mesh VPN built on the open-source WireGuard protocol. Instead of the slow, painful corporate VPN most companies dislike, Tailscale connects a team's devices, servers, containers, and cloud resources into a single private network, a "tailnet", where each machine can reach the others directly, secured by identity-based access control. On top of WireGuard it adds the hard parts: NAT traversal so devices connect peer-to-peer through firewalls, a coordination and control plane, access-control policies (ACLs), and zero-trust network access (ZTNA). Developers and IT teams love it for how quickly it makes secure remote access, hybrid-cloud connectivity, and machine-to-machine networking just work, and it is increasingly used to connect AI and infrastructure workloads. Tailscale was founded in 2019 by a team of ex-Google engineers, Avery Pennarun (CEO), David Crawshaw, David Carney, and Brad Fitzpatrick, the last well known for creating LiveJournal and memcached. It is headquartered in Toronto, Canada, and is known for being a remote-first company. It employs roughly 177 people and has raised about $275 million in total, including a $160 million Series C in April 2025 led by Accel (with CRV, Insight Partners, Heavybit, Uncork Capital, and angels including the CEOs of CrowdStrike and Squarespace) that valued it at around $1.5 billion.
Mission & values
Make secure networking simple, connecting people, devices, and services into one private, identity-based network without the pain of a traditional VPN.
Qualifications
Tailscale hires the roles a developer-focused infrastructure and security company needs. On the technical side: software engineering across networking and systems (Go is central, plus low-level networking, distributed systems, clients across platforms, and cloud/infra), security engineering, SRE and platform, plus product management, design, and developer-facing roles like developer relations, technical writing, and support/solutions engineering. On the commercial side it hires sales, sales engineering, customer success, and marketing (with a strong developer-marketing bent), alongside finance, legal, and people functions. Application flow lives at tailscale.com/careers. The best part for this board: Tailscale is remote-first, so roles are genuinely remote rather than office-bound. In practice it hires primarily across Canada and the United States, with some roles open in select other countries; each posting states the eligible locations and any work-authorization requirements, so check those. Deep networking, systems, or Go experience, and a genuine feel for developer experience, are strong signals for engineering roles.
Leadership
Avery Pennarun
Co-Founder & Chief Executive Officer
Co-founded Tailscale in 2019 and leads it as CEO. A longtime engineer (previously at Google) known in open source as apenwarr and for tools like sshuttle, focused on making secure networking effortless.
David Crawshaw
Co-Founder
Co-founded Tailscale in 2019 and served as an early technical leader (CTO). Previously an engineer at Google, with deep systems and Go expertise underpinning Tailscale's architecture.
Hiring process
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1
Apply at tailscale.com careers
Browse remote engineering, security, product, design, developer relations, and go-to-market roles and submit through the Tailscale careers site. Each posting lists eligible locations (mainly Canada and the US).
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2
Recruiter screen
Confirms role fit, level, location and work authorization (eligible countries vary by posting), remote setup, and pay.
About 7 days
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3
Technical or role-specific interview
Engineering: coding (often Go), networking, and systems design. Product/design: portfolio and case. Go-to-market: a scenario relevant to a developer-led product.
About 10 days
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4
Team interviews
Conversations with the team on depth, remote collaboration, and fit for a developer-first, remote-first culture.
About 10 days
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5
Offer
Offer with base plus equity (and OTE for sales roles), aligned to role and location, in CAD or USD.
About 7 days
Funding
Awards & recognition
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Raised a $160M Series C led by Accel at a ~$1.5B valuation · 2025
Tailscale
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Remote-first secure-networking platform built on WireGuard · 2026
Tailscale
Company information
- Industry: Cybersecurity / Networking (VPN / Zero Trust)
- Location: Remote-first (HQ Toronto, Canada; hires mainly Canada & US)
- Founded: 2019
- Employees: 177
- Website: tailscale.com ↗
- LinkedIn: Company page ↗