Tailscale

Product Engineer (Billing)

United States

Not SpecifiedCompensation
Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Software, InternetIndustries

Software Engineer - Billing

About Tailscale

Tailscale is building the new Internet 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.

Position Overview

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 a third-party service, 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.

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, Orb) 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, 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.

Compensation & Benefits

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: $163,000 - $204,000 USD

Skills

Billing Systems
Stripe
Orb
Usage-based Billing
Subscription Billing
Software Development
Product Lifecycle Management
UX/UI Collaboration
Asynchronous Communication
Automation Tools
Data Integrity
Reconciliation
Reporting

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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