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Tailscale

Billing 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

The Billing Engineer at Tailscale will be responsible for developing and maintaining the billing system, integrating with third-party services, and ensuring accurate tracking and reporting of customer usage data. This role involves collaborating with various teams, including UX/UI designers and product managers, and requires a strong focus on backend software engineering, particularly in billing and financial systems.

Our read on this posting2.8out of 5
benefits
4/5
freshness
1/5
career value
4/5
role clarity
5/5
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 in backend software engineering, with a strong focus on billing, payments, or financial systems.
  • Deep knowledge of SaaS billing models, including subscriptions, usage-based pricing, proration, discounts, and entitlements.
  • Proven experience integrating with third-party billing platforms such as Stripe, Metronome, Orb, Zuora, etc.
  • Experience designing and managing distributed systems, microservices, and event-driven architectures.
  • Proficient with SQL and data modeling, especially for financial and usage data.
  • Solid understanding of APIs and experience building or integrating internal billing APIs.

Nice to have

  • 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.
  • Paid time off and a flexible PTO program.
  • A build-your-own home office setup with a company-owned laptop and reimbursement for home internet.
  • Paid parental leave program with top-ups for birthing and non-birthing parents.

Worth weighing

  • The role requires comfort with asynchronous work and collaboration in a fully remote environment.
  • No specific mention of the tech stack beyond Go and SQL, which may imply a focus on legacy systems if not modernized.
  • The salary range is provided, but individual offers may vary based on experience and skill set.
  • The emphasis on integrating with third-party services may require ongoing adaptation to external platforms.

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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