Start searching

Tailscale jobs

36 live jobsTechnology & Software201-500Toronto, CanadaFounded 2019tailscale.com
See 36 open roles

Tailscale is a cloud-based VPN service that makes it easy to connect your devices securely, no matter where they are. It uses WireGuard to create a private network, offering a modern and user-friendly approach to secure remote access. Tailscale simplifies network management, allowing users to instantly connect servers, laptops, and phones as if they were on the same local network.

Live jobs36
Median salary$153kAdvertised, typical range $143k - $181k
Top locationRemote (United States)+4 other locations
Work mode19% hybrid

Open roles at Tailscale

Showing 36 of 36 live jobs

Let Haystack apply for you
Auto Apply finds the jobs that fit you and sends the applications for you. Setup takes about 2 minutes.
Try Auto Apply

How applying to Tailscale works

From 31 applications Haystack's AI agent sent to Tailscale since September 2026. Updated daily.

How do I apply for a job at Tailscale?

Tailscale takes applications through Greenhouse, on its own careers site. The form usually has about 17 fields to fill in. Haystack's AI agent can fill in and submit the form for you: upload your CV once, pick the Tailscale roles you want, and every reply lands in your Haystack inbox.

What does Tailscale's application form ask?

Besides your contact details and CV, the questions that come up most on Tailscale's form are: "We're always curious - have you used Tailscale before?"; "Why are you interested in joining Tailscale? Thoughtful responses are encouraged."; "Will you now or at any point in the future require visa sponsorship to work in the United States?"; "Are you located in or willing to relocate to the United States?"; "Do you have experience owning or building the operating rhythms for an Engineering, Product, and Design (EPD) org, things like planning cycles, recurring review".

How long does Tailscale take to reply to applications?

When Tailscale replies to an application sent through Haystack, the first reply (an interview invite, a decision or a request) usually arrives within about 16 days. So far 50% of applications sent more than two weeks ago have had a reply. Based on 7 replies.

Let Haystack apply for you