Tailscale
Category: AI Infrastructure
A Zero Trust identity-based connectivity platform that replaces legacy VPN, SASE, and PAM, connecting remote teams, multi-cloud environments, CI/CD pipelines, Edge & IoT devices, and AI workloads. Tailscale was founded in 2019. The company is led by Avery Pennarun. Based in Toronto, Canada. Team size: 101-500. Total funding raised: $275M total (all rounds). Latest round: Series C ($160M, Apr 2025 led by Accel). Key investors include Accel, CRV, Insight Partners, Heavybit, Uncork Capital.
- Founded
- 2019
- Headquarters
- Toronto, Canada
- Team size
- 101-500
- Total funding
- $275M total (all rounds)
Value proposition
Delivers simple, secure, zero-trust networking with seamless integration to existing identity providers, eliminating the need for complex firewall setups.
Products and solutions
Tailscale VPN (Mesh VPN), Tailscale SSH, MagicDNS, Tailscale Funnel, Exit Nodes, Access Controls (ACLs), Kubernetes Operator, Configuration Audit Logging, Tailnet Lock, Docker Desktop Extension, Aperture (AI governance platform), Taildrop (P2P file sharing)
Unique value
Emphasis on extreme ease-of-use with zero-configuration setup, leveraging a peer-to-peer WireGuard mesh network and an identity-centric access model.
Target customer
Developers, IT teams, SMBs to Enterprises, and individuals seeking secure remote access and simplified networking.
Industries served
Technology, Software Development, IT Services, Finance, Healthcare, Education, General Business, Individual/Homelab users
Technology advantage
Combines the high performance and security of WireGuard with a user-friendly interface, seamless identity provider integration, a strong open-source community, and a product-led growth approach.
How they differentiate
Focuses on simplicity, excellent developer experience, and a robust free tier combined with pure peer-to-peer WireGuard-based networking.
Main competitors
Zscaler Private Access, Palo Alto Networks (Prisma Access), Cloudflare Access, ZeroTier, Netmaker, OpenVPN Cloud
Key partnerships
Identity Providers (Okta, Google Workspace, Microsoft Entra ID, GitHub, etc.), Cloud Providers (AWS, Azure, GCP), Technology partners (e.g., Docker, Kubernetes ecosystem)
Notable customers
Instacart, Hugging Face, Cribl, Mercury, Cohere, Mistral, Groq, Perplexity, Duolingo, Nvidia, Microsoft, Telus
Major milestones
Founded (2019), Raised Seed Round ($3M, Apr 2020), Raised Series A ($12M, Nov 2020), Raised Series B ($100M, May 2022), Raised Series C ($160M, Apr 2025), Launched Aperture AI governance platform (Feb 2026), Acquired Border0 for PAM capabilities (Mar 2026)
Growth metrics
As of Nov 2025, 20,000+ paying customers and 1M+ monthly active users. Revenue in tens of millions, growing at accelerating rate. 14th on Deloitte's Fast 50 with 3,299% three-year revenue growth through 2024.
Market positioning
Well-positioned as a leading Zero Trust identity-based connectivity platform, replacing legacy VPN, SASE, and PAM. Particularly favored by AI companies, developers, and enterprises. Achieved $2B CAD valuation and 20,000+ paying customers as of late 2025.
Geographic focus
Global, with particularly strong adoption in North America and other major tech hubs worldwide.
Patents and IP
No specific patents disclosed; relies on open-source innovations like WireGuard.
About Avery Pennarun
Avery Pennarun is a seasoned entrepreneur and engineer with a deep background in networking and software development. He co-founded Tailscale, a zero-config VPN solution, and serves as its CEO. Before Tailscale, he consulted for Alphabet's senior leadership and led the gigabit WiFi and platform analytics team at Google Fiber. His career began with an early passion for networking, building a Linux driver as a teenager and starting a company in college to help small businesses share dial-up connections. His philosophy emphasizes simplicity in product design and a bottom-up growth strategy, focusing on developers and small teams.
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Official website: https://tailscale.com