PitchMeAI Jobs
Tailscale

Windows Engineer

Tailscale · Remote (United States)

Posted about 2 months ago

or apply directly on Tailscale's site. We never take the application ourselves.

Is this posting real?

This role has been open
72 days
Tailscale's roles stay open a median of 76 days
Reposted
No
Salary listed
No
2% of Tailscale's roles list one
Ghost-job risk at Tailscale
high
60 stale, 2 reposted of 60 open
Hiring momentum
113 roles opened in the last 90 days
↑ up vs. the prior 90 days
Last confirmed on the employer's board
2026-10-22

Measured from postings appearing on and disappearing from Tailscale's own greenhouse board since 2026-08-03. Full hiring picture for Tailscale.

About this role

As a Windows Engineer at Tailscale, you will develop and maintain the Windows client of the Tailscale product, focusing on modern UI frameworks and backend services. You will work with a mix of C#, XAML, and Go, while also ensuring compatibility with older Windows versions. The role requires collaboration with a remote engineering team and involves implementing new features and optimizing existing ones for the Windows platform.

Our read on this posting2.8out of 5
benefits
5/5
freshness
1/5
career value
4/5
role clarity
4/5
pay transparency
0/5

Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Tailscale as an employer.

What you need

  • Four or more years of experience in software development
  • Strong understanding of software development principles, capabilities, and limitations of the Windows platform
  • Proficiency in C# and modern native UI frameworks (WinUI/UWP/WPF)
  • Experience with general networking concepts - DNS, VPNs, IP Networking, routing, etc.
  • Excellent written and verbal communication skills
  • Ability to give and process constructive feedback, as well as work independently

Nice to have

  • Experience with WinUI 3 and Windows App SDK
  • Experience developing native Windows applications and services
  • Familiarity with Windows networking stack and Windows Filtering Platform
  • Familiarity with Windows security model, session isolation, access tokens and related concepts
  • Proficiency in Go

What you get

  • Base salary range of $143,000 — $179,000 USD
  • Equity incentive plan
  • Comprehensive group benefits with no waiting period for health, vision, dental, and more
  • Employer-funded retirement contributions matching dollar-for-dollar up to 0.75% of eligible compensation
  • Annual professional development budget of $1500 USD
  • Flexible paid time off program

Worth weighing

  • No specific mention of the tech stack beyond C#, XAML, and Go, which may indicate a focus on legacy or less modern technologies
  • The role requires comfort with asynchronous work, which may not suit everyone
  • The company is fully remote, which may require self-motivation and discipline

Summarised from Tailscale's posting. Read the full original.

Listed by Tailscale on their greenhouse job board, last confirmed open on 2026-10-22. PitchMeAI is not the employer.

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