Own the product strategy and roadmap for Tailscale's entitlements, plans, and billing infrastructure
Own the Stripe integration and payment processing stack
Build and manage the usage data ingestion pipeline and APIs
Design the UX for usage reports and invoices
Define and manage entitlements and plan structures
Own enterprise billing workflows
Partner with the Growth PM to build shared metering and event data infrastructure
Partner with Finance and GTM to develop pricing and packaging changes
Define and track key billing metrics

Requirements

4+ years in a product role, with direct experience owning billing, payments, pricing, or monetization systems at a SaaS or technology company
Understanding of billing systems architecture
Experience with pricing and packaging strategy
Experience with data analytics tools (e.g., SQL, Looker, Snowflake)
Strong product taste
Ability to explain complex billing and pricing concepts to both technical and non-technical stakeholders
Able to move fast, build your own context, and drive decisions without waiting to be directed.

Benefits

An inclusive, flexible environment where you can be your authentic self.
A competitive total compensation package.
Comprehensive group benefits with no waiting period.
Remote first company—most of our teams work fully remotely.
Connect with other Tailscalars IRL.
Support for your personal and professional development.
Paid time off and a healthy work-life integration.
A build-your-own home office setup.
Generous parental leave program from your first day.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

billing systems architecturepayment processingdata analyticsSQLLookerSnowflakeAPI developmentUX designusage data ingestionpricing strategy

Soft Skills

strong product tastecommunicationdecision-makingcollaborationability to explain complex conceptsorganizational skillsadaptabilityproblem-solvingstakeholder managementself-direction