Tailscale

Infrastructure Engineer

Tailscale · Remote (Canada)

Posted about 3 months ago

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

Is this posting real?

This role has been open
80 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 an Infrastructure Engineer at Tailscale, you will be part of a team responsible for designing, building, and maintaining core software components that enhance the company's infrastructure. Your role will involve supporting internal business units, improving observability, automating processes, and collaborating with various stakeholders to ensure efficient operations. You will also be expected to analyze system performance and participate in incident response.

Our read on this posting2.6out of 5
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

  • Experience with CI/CD, secrets management, infrastructure as code, and observability
  • Experience with distributed systems
  • Experience with operating managed services in a cloud environment (preferably AWS)
  • Experience with operating Kubernetes in production
  • Familiarity with networks (IP addressing, routing, etc.)
  • Ability to give and process constructive feedback

Nice to have

  • Experience with Go programming language
  • Flexibility to adjust to the dynamic nature of a startup

What you get

  • Comprehensive group benefits with no waiting period including health, vision, dental, and more
  • Employer-funded retirement contributions matching dollar-for-dollar up to 0.75% of eligible compensation
  • $1500 USD annually for professional development
  • Flexible paid time off program
  • Build-your-own home office setup with a $500 USD workstation customization allowance
  • Paid parental leave program with top-ups for new parents

Worth weighing

  • No specific mention of the technology stack beyond CI/CD and cloud services
  • The role requires strong independence and self-motivation due to the fully remote nature of the company

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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