About this role.
Tailscale is seeking a senior-level Billing Engineer to build and operate core SaaS billing capabilities in a fully distributed engineering organization. The role focuses on subscription and usage-based billing, including metering, pricing, rating, reconciliation, reporting, and integrations with platforms such as Stripe and Metronome. This engineer will own work across the product lifecycle, collaborate closely with product, finance, sales, support, and design partners, and improve reliability across the billing pipeline. Strong backend systems experience, SQL/data modeling expertise, API design skills, and the ability to work independently in an asynchronous startup environment are central to success.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
4/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would define immutable usage events with clear idempotency keys, timestamps, account identifiers, and versioned schemas. Events would be validated, persisted durably, aggregated into billable periods, and rated using versioned pricing rules. I would include reconciliation against source systems, audit trails, replay capability, and monitoring for late, duplicate, or missing events before invoice finalization.
I would isolate provider-specific behavior behind an internal billing interface, use idempotency keys for all write operations, and persist external identifiers and request outcomes for auditability. Webhooks would be signature-verified, deduplicated, and processed asynchronously with retries and dead-letter handling. I would also establish reconciliation jobs to identify and resolve differences between internal records and provider records.
I would model plan changes as effective-dated events and calculate charges from the exact active intervals, rather than overwriting subscription state. Pricing and discount rules should be versioned, deterministic, and independently testable so historical invoices can be reproduced. Entitlements should be derived from the same authoritative subscription state, with clear handling for pending changes, grace periods, and cancellation.
I would first contain the issue by pausing the affected rating or invoicing workflow where appropriate and determining the impacted customer and invoice population. I would compare source usage, pricing-rule versions, aggregation outputs, and provider-side charge records to isolate the root cause. After correcting customer balances or issuing credits, I would document the incident, add targeted tests and alerts, and implement preventative controls such as reconciliation thresholds or approval gates for pricing changes.
I translate implementation choices into customer, revenue-recognition, operational, and delivery implications. For example, I would explain how a custom pricing exception affects invoice accuracy, support workload, reporting, and long-term maintainability, then present viable options with scope, risks, and timelines. I document decisions clearly and ensure stakeholders agree on ownership, acceptance criteria, and rollout monitoring.
About Tailscale
Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We’re building a future for the Internet that’s easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we’re backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
About the Role
We’re seeking a highly skilled and motivated Software Engineer to join our growing team. You will work as part of the engineering team to:
- Deliver projects related to pricing plans and billing
- Develop our billing integration with third party services, strengthening our end-to-end billing experience.
- Take ownership of the entire product lifecycle, from writing code to product ideation and strategic decision-making.
- Work closely with UX/UI designers and product managers to shape features.
Because we’re an early-stage and fully remote company, we’re looking for a strongly motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.
Key Responsibilities
- Work as part of a team of engineers to design, build, test, and document core billing software components.
- Integrate with third-party billing platforms (e.g., Stripe, Metronome) as needed
- Develop metering, pricing, and rating logic for usage-based and subscription billing models.
- Ensure accurate tracking and reporting of customer usage data.
- Monitor and maintain billing systems to ensure high availability and data integrity.
- Build automation tools for recurring billing tasks, reconciliation, and reporting.
- Collaborate with product, sales, and finance teams to support custom billing requirements.
- Work closely with finance, product, support, and engineering teams to support accurate billing, revenue reporting, and customer inquiries.
- Act as a technical expert in billing-related discussions and planning.
- Champion engineering excellence by driving code quality, architectural reviews, and design documentation.
- Provide technical leadership and mentorship to other engineers, fostering a culture of learning and knowledge sharing.
- Establish observability, alerting, and error handling across the billing pipeline to ensure high availability and responsiveness.
- Lead incident response and root cause analysis for billing-related issues.
What We Are Looking For
- 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, or building custom billing systems.
- 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.
- Strong proficiency in Go, or comfortable writing production-quality code in another language and eager to work with Go
- Flexibility to adjust to the dynamic nature of a startup.
- Excellent written and verbal communication skills.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale’s compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire’s base salary. Individual offers may vary based on experience and skill set.
US Pay Range
$143,000—$179,000 USD
Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!
What We Offer
- An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
- Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
- Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
- A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale’s talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
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