Own the product strategy and roadmap for Tailscale's entitlements, plans, and billing infrastructure
Own the Stripe integration and payment processing stack — plan selection, payment UX, subscription lifecycle management
Build and manage the usage data ingestion pipeline and APIs that power metering, usage reporting, and usage-based billing
Design the UX for usage reports and invoices — making billing data clear and trustworthy for both self-serve and enterprise customers
Define and manage entitlements and plan structures that map Tailscale's pricing and packaging to the features customers can access
Own enterprise billing workflows, including Salesforce ↔ billing entitlement sync and custom enterprise plan management
Partner with the Growth PM to build shared metering and event data infrastructure that serves both product analytics and billing
Partner with Finance and GTM to develop and execute pricing and packaging changes, translating business strategy into product requirements
Define and track key billing metrics (expansion revenue, billing-related churn, invoice accuracy, support ticket volume) and use data to prioritize the roadmap

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 — you can have a meaningful technical conversation about metering, rating, invoicing, payment processing, and subscription lifecycle management
Experience with pricing and packaging strategy — you've shipped pricing changes and understand the cross-functional coordination required across product, finance, sales, and marketing
Experience with data analytics tools (e.g., SQL, Looker, Snowflake) and comfort using data to drive prioritization and measure outcomes
Strong product taste — you believe billing and checkout experiences deserve the same design rigor as core product features
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 processingsubscription lifecycle managementdata analyticsmeteringratinginvoicingpricing strategypackaging strategyAPI development

Soft Skills

communicationcross-functional coordinationproduct tastedecision-makingexplanation of complex conceptsorganizational skillsability to work independentlyadaptabilitystrategic thinkingdata-driven prioritization