Tailscale
Tailscale sells private networking software that replaces corporate VPNs with a simpler setup. The 360-person company raised $276M in a Series C in April 2025.
The growth story
Tailscale grew from 29 to 360 employees between 2021 and 2026, raising $276M along the way, most recently a Series C in April 2025.
About
Tailscale provides software that lets teams create secure private networks without complex VPN setups. It targets companies that want to connect remote workers and cloud services with lower latency than traditional VPNs.
The company has grown to 360 employees since its 2019 founding, with recent funding suggesting rapid expansion. Its $276M Series C in April 2025 indicates strong investor confidence in its approach to enterprise networking.
Founders and leadership
Sales is the largest function with 49 employees, suggesting a focus on commercial growth. The company has a young workforce with a median tenure of just one year, typical of fast-growing startups.
The Tailscale org chart
Avery Pennarun (Co-founder and CEO) leads 56 mapped leaders with 10 direct reports. Click +N to expand a team; names link to the person’s public profile.
Departments, and which ones grew
Headcount by function: Engineering 108 (+46% YoY), Sales 38 (+58% YoY), Information Technology 20 (+54% YoY), Marketing 20 (+67% YoY), Human Resources 20 (+186% YoY), Business Development 16 (+60% YoY).
Talent flow
Tailscale recruits heavily from networking and infrastructure companies, with Google (14 hires), Cloudflare (13), and HashiCorp (13) as top sources. Alumni frequently join infrastructure startups like Crusoe and Microsoft.
Most common previous employers of Tailscale staff: Google (14), Cloudflare (13), HashiCorp (13), DigitalOcean (10), Pulumi (9), Gong (8). Former Tailscale employees most often moved to Crusoe (3), Oblique (2), Microsoft (2), 1Password (2), Meta (2), exe.dev (2).
Alumni worth knowing
The Tailscale mafia
Five alumni-founded companies exist, including Oblique and exe.dev, each with multiple former Tailscale staff members. This suggests strong technical talent retention in the networking space.
5Maya Kaczorowski, was Chief Product Officer until 2024Josh Bleecher Snyder, was Software until 2022Jordan Glasner, was Head of Product until 2025Samantha Griffith, was Graphic Designer until 2024Hiring now
Web traffic
Traffic mix: 62% direct, 33% search, 1% social, 1% paid.
What this company is made of
Most common skills at Tailscale: Leadership (104), Python (Programming Language) (89), Customer Service (80), Management (79), Microsoft Office (78), Linux (78), JavaScript (71), Project Management (67).
Where the team actually sits
Tailscale people are concentrated in California, United States (27), Ontario, Canada (23), Colorado, United States (19), British Columbia, Canada (15).
Search footprint
Tailscale attracts about 15,939 organic search visits a month, traffic worth roughly $99K a month if bought through ads. It gained 3,050 ranking keywords and lost 2,369 in the last period.
What employees say
- Compensation
- 4.40 / 5
- Career opportunities
- 4.20 / 5
- Senior management
- 4.00 / 5
- Work-life balance
- 4.40 / 5
Frequently asked
Tailscale has 360 employees as of September 2026.
Tailscale has raised $276M in total, most recently a Series C round in April 2025.
Tailscale was founded in 2019 by Avery Pennarun, David Carney, David Crawshaw.
Avery Pennarun (Co-founder and CEO) sits at the top of Tailscale's reporting structure, with 10 direct reports.
The most common previous employers of current Tailscale staff are Google (14 people), Cloudflare (13 people), HashiCorp (13 people).
Former Tailscale employees most often move to Crusoe (3), Oblique (2), Microsoft (2).
At least 5 companies have a founder who previously worked at Tailscale, including Oblique, exe.dev, Techaro.
Tailscale attracts about 15,939 organic search visits a month, worth roughly $99K a month in equivalent ad spend.
The most common skills among Tailscale staff are Leadership, Python (Programming Language), Customer Service, Management, Microsoft Office.
Tailscale staff are concentrated in California, United States (27), Ontario, Canada (23), Colorado, United States (19).
Tailscale has about 108 people in Engineering, up 46% over the past year, as of September 2026.
Tailscale has about 38 people in Sales, up 58% over the past year, as of September 2026.
Computed from 241 current and 108 former Tailscale profiles, as of September 2026. Source: Crustdata.
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