Tailscale

Zero-Config VPN & Mesh Networking — Making Networking Just Work

The consensus on Tailscale: Choose Tailscale if you want same-pay-worldwide, exceptional WLB, and a deeply technical culture — but expect limited career progression and growing pains.

2019
Founded
Toronto, ON
Headquarters
~290
Employees
~$1.5B
Valuation (2024)
Culture Overview

What it's really like to work at Tailscale

Founded in 2019, Tailscale builds a zero-config VPN and mesh networking platform powered by WireGuard. The culture is deeply engineering-driven and remote-first, with same pay worldwide regardless of location. Expect a nerdy, intellectual environment led by a technically brilliant CEO, with strong emphasis on work-life balance, written communication, and genuine diversity and inclusion.

Remote-Friendly Work-Life Balance Strong Comp & Equity Engineering-Driven Diverse & Inclusive Transparent
Glassdoor Ratings

Tailscale Glassdoor Ratings & Employee Reviews

4.4
Overall Glassdoor Score
Based on 7 reviews
Culture & Values 4.3
Compensation & Benefits 4.8
Senior Management 4.1
Career Opportunities 3.0
Work-Life Balance 4.5
Overall Rating 4.4
79% Recommend to a Friend
100% CEO Approval (Avery Pennarun)
Employee Review Themes

Working at Tailscale: Pros & Cons

✓ What employees love

  • ✓ Same pay worldwide with 26 weeks parental leave and genuine work-life balance (4.5/5)
  • ✓ Brilliant, nerdy CEO who deeply understands the tech — culture is intellectual and respectful
  • ✓ D&I rated 4.7/5 — the highest diversity score in our database
  • ✓ Compensation & benefits rated 4.8/5 — competitive pay regardless of location
  • ✓ WireGuard-based technology with real technical depth — not just another SaaS app

✗ What could be better

  • ✗ Career opportunities rated 3.0/5 — limited paths for growth at a mid-sized company
  • ✗ Middle management still developing — some growing pains as the org scales
  • ✗ Some concerns about PTO policies and time-off enforcement
  • ✗ Only 79% recommend — lower than you'd expect for a company with these benefits
Engineering Culture

How the engineering team works

Tech Stack

Go TypeScript React WireGuard Linux Networking

Open Source & Research

WireGuard-based, with open-source contributions. Tailscale publishes detailed networking research and maintains an active blog on mesh networking, DERP relays, and NAT traversal.

Engineering Blog

Deep technical blog covering WireGuard, NAT traversal, DERP, and networking protocols. Read the blog →

Team Structure

Distributed globally with same pay everywhere. Small, autonomous engineering teams. Strong emphasis on written communication and documentation.

Open Positions

Join the Tailscale team

Explore featured roles below, or browse all 36 open positions on the full jobs board.

See all 36 Tailscale jobs →