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)
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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

... open positions.

Community Sentiment

What the community says about Tailscale

Mostly Positive 5 mentions from Hacker News & Reddit · Updated 2026-04-10
“Funny, I had a similar idea this morning in the shower. I was thinking about how distributed digital infrastructure could be achieved in practice. Running some music streaming and photo server on an old laptop at home that I access via tailscale has proved surprisingly smooth.”
Hacker News wouterjanl · 2026-04-10 View thread →
“my experience with RustDesk + Tailscale is really good. when i only needed windows remote devices, the Windows Remote Desktop over Tailscale is great. I used RustDesk for access to macOS and Android devices (all over Tailscale) and works great too. No complaints really.”
Hacker News raihansaputra · 2026-04-01 View thread →
“My work guest WiFi network allows only IPv4 HTTPS on port 443 and their their own DNS. Everything else, including ICMP (ping) is blocked. Tailscale barely works as any persistant connection is dropped after 2-3 minutes.”
Hacker News mrsssnake · 2026-03-31 View thread →
“Great to see. It’ll be great to democratize access to remotely using cli coding agents.I’ve been iterating the past few months on a solution to use Claude Code on my phone while it runs on my laptop and it’s a lot of moving parts: Tailscale, git worktrees, tmux, an always-on...”
Hacker News cadamsdotcom · 2026-02-12 View thread →

Sentiment data refreshed daily from public Hacker News and Reddit discussions. See all company profiles →

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