Is Tailscale hiring right now?

Yes. Tailscale has 53 open roles listed as of October 29, 2026.

Where is Tailscale hiring?

The most open roles are in Singapore (1).

How much does Tailscale pay?

Across open roles that list pay, the average advertised base salary at Tailscale is $170k a year, and the highest is $350k.

Where is Tailscale headquartered?

Tailscale is headquartered in Toronto, Ontario, Canada and was founded in 2019.

Avery Pennarun, Co-Founder & CEO, is at the top of Tailscale's org chart.

How do I apply for a job at Tailscale?

Pick a role on Tailscale's TheJobsMap page and select Apply. Every listing links to the original posting on Tailscale's own careers site, so you apply directly with the employer.

Tailscale jobs and careers

Toronto, Ontario, Canada. Jobs in Toronto

As of October 29, 2026, Tailscale has 53 open roles.

tailscale.com LinkedIn @tailscale

See 53 open roles

Headquartered in Toronto

53Open roles

2Posted in the last 7 days

$170kAverage listed base pay

$350kHighest listed base pay

About Tailscale

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Founded in 2019 by Avery Pennarun, David Carney and David Crawshaw.

Cyber Security Information Technology Infrastructure Network Security

Founded: 2019
Employees: 51 to 100
Total funding: $115.5M
Headquarters: Toronto
Hiring in: 1 city

Leadership

The top of Tailscale's org chart, with how many people report into each leader.

Avery Pennarun

Co-Founder & CEO

128 reports

Kevin Kotecki

President, interim

62 reports

Andrew Mitchell

VP Of Engineering

22 reports

Sam Linville

Interim Head Of Product

13 reports

Saloni D.

Vice President, People

7 reports

Ross Kukulinski

VP Product & Interim VP Engineering

4 reports

Christian Fatoohi

VP Of Finance

3 reports

Will Moore

Head of Corporate Communications

2 reports

Grace Lin

Senior Vice President Operations

1 report

Board

Rebecca Liu-Doyle

Advisor

Reid Christian

Advisor

Joseph Ruscio

Advisor

Shelly Glennon

Advisor

Andy Mcloughlin

Advisor

Abel Mathew

Advisor

Open roles at Tailscale 53

Tailscale jobs: common questions

Is Tailscale hiring right now?: Yes. Tailscale has 53 open roles listed as of October 29, 2026.
Where is Tailscale hiring?: The most open roles are in Singapore (1).
How much does Tailscale pay?: Across open roles that list pay, the average advertised base salary at Tailscale is $170k a year, and the highest is $350k.
Where is Tailscale headquartered?: Tailscale is headquartered in Toronto, Ontario, Canada and was founded in 2019.
Who leads Tailscale?: Avery Pennarun, Co-Founder & CEO, is at the top of Tailscale's org chart.
How do I apply for a job at Tailscale?: Pick a role on Tailscale's TheJobsMap page and select Apply. Every listing links to the original posting on Tailscale's own careers site, so you apply directly with the employer.