Startups > Tailscale

Tailscale

Tailscale replaces VPNs with Zero Trust mesh networking for secure team connectivity.

Series C $275M total Founded 2019 Toronto, Ontario 187 employees

Tailscale is a Zero Trust identity-based connectivity platform that replaces legacy VPNs, SASE, and PAM solutions by enabling secure private networks through peer-to-peer mesh networking built on WireGuard. It connects remote teams, multi-cloud environments, CI/CD pipelines, Edge/IoT devices, and AI workloads without requiring port forwarding, firewall rule changes, or complex VPN configurations. The platform uses advanced NAT traversal (STUN/ICE) and DERP relay protocols to establish direct encrypted connections across any network topology. Trusted by 10,000+ paid business customers including Fortune 500 companies, AI startups like Mistral and Hugging Face, and enterprises like Duolingo, Instacart, and Revolut.

Problem solved

Organizations waste significant engineering time and resources configuring and maintaining legacy VPNs, managing firewall rules, and dealing with NAT traversal issues instead of focusing on core business infrastructure.

Target customer

Mid-market to enterprise organizations with distributed teams, multi-cloud infrastructure, CI/CD pipelines, or edge deployments requiring secure private connectivity without traditional VPN complexity. Includes Fortune 500 companies, AI startups, and high-growth SaaS companies.

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Founders

Avery Pennarun

CEO & Co-Founder

Former Google engineer who founded Net Integration Technologies (Nitix) in 2001 and wrote the first VPN 'Tunnel Vision' in 1997; early experience running systems at an ISP in Thunder Bay.

David Crawshaw

CTO & Co-Founder

Former Google engineer with deep networking expertise from the 1990s LAN era.

David Carney

Co-Founder & Chief Strategy Officer

Co-founder and former CFO of Format.

Brad Fitzpatrick

Co-Founder

Former Google engineer.

Funding history

Seed $3M April 2020 Led by Unknown · Unknown

Series A $12M November 2020 Led by Accel · Heavybit, Uncork Capital

Series B $100M May 2022 Led by CRV · Insight Partners

Series C $160M April 2025 Led by Accel · CRV, Insight Partners, Heavybit, Uncork Capital, George Kurtz (CrowdStrike CEO), Anthony Casalena (Squarespace CEO)

Total raised: $275M

Industries

Information Technology Cyber Security Infrastructure Network Security

Pricing

Seat-based pricing: Free Personal plan (6 users per tailnet), Standard at $6/user/month (annual) or $7/user/month (monthly), Premium for heavy usage, and Enterprise with custom pricing for 200+ users including dedicated support and SLAs. Special discounts available for open source projects, charities, nonprofits, and educational institutions (50% off).

Notable customers

Revolut, Instacart, Mercury, Duolingo, Airbus, Mistral, Hugging Face, Cohere, General Motors, AWS

Integrations

Stripe, Google Workspace, Google Analytics, Segment, Sentry, Google Tag Manager, Heap

Tech stack

parcel Segment (Customer data platform) Heap (Analytics) Google Analytics (Analytics) Sentry (Issue trackers) TornadoServer (Web servers) Google Workspace (Email) Stripe (Payment processors) Google Tag Manager (Tag managers)

Website

tailscale.com/

Competitors

Cisco AnyConnect

Traditional client-based VPN with higher complexity and maintenance overhead; lacks Zero Trust architecture and modern mesh networking capabilities.

Cloudflare Zero Trust

Broader SASE platform with DNS filtering and web security; Tailscale is more focused on lightweight peer-to-peer connectivity without internet-scale overhead.

Zscaler Private Access

Enterprise-grade SASE solution with more comprehensive security services; Tailscale optimizes for simplicity and direct connectivity over feature breadth.

WireGuard (open source)

Tailscale provides managed orchestration, identity-based access control, and Zero Trust features on top of WireGuard; WireGuard itself requires manual configuration.

Why this matters: Tailscale has achieved unicorn status ($1.5B valuation) by solving a fundamental problem that affects every distributed organization—VPN complexity. Founded by four Google engineers with deep networking expertise, the company has built an elegant solution that replaces legacy enterprise infrastructure with modern Zero Trust principles, attracting 10,000+ customers including AI leaders and Fortune 500 companies. The April 2025 Series C ($160M) with backing from major VCs and strategic angels (Squarespace CEO, CrowdStrike CEO) signals continued strong demand for simpler, identity-based connectivity.

Best for: Remote-first companies, multi-cloud deployments, AI/ML teams, and enterprises needing Zero Trust connectivity without the complexity of traditional VPNs or the overhead of internet-scale infrastructure.

Use cases

Securing Remote Development Teams

Engineering teams can securely access internal dashboards, build systems, and databases from anywhere without VPN clients or firewall rule management. Developers connect directly to each tailnet device with encrypted tunnels that work across any network, including restrictive corporate WiFi and home networks behind multiple NATs.

Multi-Cloud CI/CD Pipeline Security

CI/CD systems spanning AWS, GCP, and Azure can establish direct secure connections to private infrastructure without exposing services to the internet. Build agents automatically join the tailnet and authenticate based on identity, eliminating the need for complex firewall rules or static IP allowlists.

IoT & Edge Device Management

Distributed IoT devices and edge computing nodes connect directly to central management systems and cloud infrastructure with automatic NAT traversal. Organizations avoid costly relay infrastructure and port forwarding while maintaining Zero Trust access control based on device identity.

AI Workload Secure Connectivity

AI startups and teams connect training clusters, inference endpoints, and data pipelines across regions without opening ports or managing VPN configurations. Identity-based access ensures only authorized services can communicate while maintaining low-latency direct connections.

Alternatives

Cisco AnyConnect Choose if you need legacy enterprise VPN with extensive compliance certifications; Tailscale is better for modern, distributed teams prioritizing simplicity.

Cloudflare Zero Trust Choose if you need comprehensive SASE with DNS security and web filtering; Tailscale is better for organizations focused purely on secure connectivity and peer-to-peer networking.

WireGuard (open source) Choose if you want complete control and can manage manual configuration; Tailscale is better if you need managed orchestration, identity-based access, and Zero Trust without operational overhead.

FAQ

What does Tailscale do? +

Tailscale is a Zero Trust identity-based connectivity platform that replaces legacy VPNs by enabling secure peer-to-peer mesh networking between devices. It uses WireGuard encryption and advanced NAT traversal to establish direct connections across firewalls and complex networks without port forwarding or firewall rule changes. Organizations use it to securely connect remote teams, multi-cloud infrastructure, CI/CD pipelines, and IoT devices.

How much does Tailscale cost? +

Tailscale offers a free Personal plan for up to 6 users, Standard pricing at $6/user/month (billed annually) or $7/user/month (monthly), Premium for heavy usage, and custom Enterprise pricing for 200+ users. Pricing is seat-based with automatic scaling. Open source projects, nonprofits, and educational institutions receive 50% discounts.

What are alternatives to Tailscale? +

Cisco AnyConnect (traditional enterprise VPN), Cloudflare Zero Trust (broader SASE platform), and open source WireGuard (manual configuration). Tailscale differentiates through simplicity, identity-based access control, and managed orchestration without internet-scale overhead.

Who uses Tailscale? +

Tailscale serves 10,000+ paid business customers ranging from startups to Fortune 500 companies. Notable customers include Duolingo, Instacart, Revolut, Airbus, Mistral, Hugging Face, Cohere, and General Motors. Primary users are distributed engineering teams, multi-cloud deployments, AI/ML startups, and enterprises requiring Zero Trust connectivity.

How does Tailscale compare to Cloudflare Zero Trust? +

Both offer Zero Trust architecture, but Cloudflare Zero Trust is a broader SASE platform with DNS filtering, web security, and gateway capabilities. Tailscale is more focused on lightweight peer-to-peer connectivity and is designed for organizations that don't need internet-scale infrastructure overhead. Tailscale's strength is simplicity and direct device connections; Cloudflare's strength is comprehensive security services.