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. Your role involves collaborating with a remote engineering team to implement new features, optimize performance, and ensure compatibility across Windows versions. You will also contribute to cross-platform code and participate in testing efforts.
- benefits
- 4/5
- 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 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
- Equity incentive plan
- Comprehensive group benefits with no waiting period for health, vision, dental, and more
- Employer-funded retirement contributions
- Annual budget for professional development
- Flexible paid time off program
Worth weighing
- Remote-first company with some roles requiring in-office collaboration
- Salary range provided but individual offers may vary based on experience and skill set
- Focus on Windows platform may limit exposure to other technologies
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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