Billing Engineer

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 design