About Tailscale
What is Tailscale?
Tailscale makes software for connecting people, devices and services over private, encrypted networks. Its home page describes the product as "A Zero Trust identity-based connectivity platform that replaces your legacy VPN, SASE, and PAM", and its company page says "Tailscale is built on WireGuard, specifically wireguard-go." The company states it was founded in 2019 ("Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.") and says it raised a $160 million USD Series C in April 2025, led by Accel. The home page says "50,000 businesses choose Tailscale", and its customer stories feature Instacart, Cribl and Mercury. In March 2026 the company announced that Border0, a Vancouver-based startup in "Privileged Access Management", had joined it.
Where will I work?
Tailscale describes itself as a fully remote company. Its careers page says "Most of us work wherever there’s wifi, some teams (hi, Sales) pop into an office a few days a week to sync with plenty of opportunities to co-work" and "We’re located in Canada, the United States and the United Kingdom." On 13 November 2026 its Greenhouse board listed 74 adverts: 63 remote (28 for Canada, 32 for the United States, 2 for the United Kingdom and 1 for Singapore) and 11 hybrid Sales roles in Toronto, Vancouver, Denver and San Francisco that ask for three days a week in the office. Most roles are posted once per country, each with that country's pay range, so the same title often appears twice. Two Enterprise Account Executive adverts are remote but tied to a metro area ("Location: Remote, but based in or near San Francisco"). The adverts add that "Some roles require in-office collaboration depending on team needs", and offer a co-working programme for people who want a desk away from home.
What is the Tailscale team like?
The company page lists Small is beautiful among its guiding principles: "We don’t believe in huge teams or huge clusters." Teams are spread across Canada, the United States and the United Kingdom (the adverts also name Singapore), and meet in person at an annual company retreat and team off-sites. The CEO, Avery Pennarun, appears on the company page and signs the funding and acquisition announcements. The careers page lists the interview steps: a recruiter interview, a hiring manager interview, "Team Interviews (2-3)" and an offer, with a technical working session added for engineering, product and design roles. The adverts say the hiring process uses AI-assisted tools and that "All hiring decisions are made by people." Some engineering, operations, marketing and strategic-projects adverts ask candidates to be comfortable working asynchronously, and two Staff Product Operations Manager adverts ask for communication "in an asynchronous, remote-first environment"; neither is a company rule on hours. A few sales, support and engineering adverts mention a "fast-paced" or "high-velocity" setting, and the Front End Engineer advert includes an on-call rotation.
Work-Life Balance
The company page says Tailscale has always been "a fully remote company with flexible working hours", and that "employees are trusted and respected to manage their time and projects around their life". The careers page lists "Flexible work hours" under "Find Work-Life Balance", and all 74 adverts say "And that flexibility in how and when you work empowers our team to integrate work and life." No advert or page reviewed states core hours or a required overlap window. A 2022 interview with the CTO adds that the team keeps "to a few close time zones". Time off is described as "Flexible paid vacation, 12 paid company holidays, and holiday closures between December 24th - January 1st", with no day count given. The careers page lists paid parental leave of 20 weeks for birthing parents and 16 for non-birthing parents, while the adverts call it "top-ups"; no page says what share of salary is paid. Sick days are described as flexible.
Perks and Benefits
- Flexible working hours: "Flexible work hours" on the careers page, and the company page's "a fully remote company with flexible working hours"
- Fully remote for most roles, with a corporate co-working programme (WeWork or similar spaces) for those who want one
- Parental leave: 20 weeks for birthing parents and 16 for non-birthing parents (pay level not stated)
- Flexible paid vacation, 12 paid company holidays and a company closure between December 24th and January 1st
- Group health benefits for you and your family with no waiting period, including health, vision and dental cover
- Employer-funded retirement contributions: the adverts say Tailscale matches contributions up to 0.75% of eligible compensation
- Equity incentive plans described as generous on the careers page
- $1500 USD a year for professional development, or mentorship, coaching and internal promotion opportunities (adverts)
- Company laptop (Mac or PC), monthly internet reimbursement and a $500 USD workstation allowance
- Annual company retreat and team off-sites
- Salary range shown on the posting (73 of 74 adverts)