Product Manager, Billing

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. They are seeking a Senior Product Manager to own Tailscale's billing and monetization infrastructure, focusing on systems that capture value through entitlements, plans, and payment processing.

Responsibilities:

• 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
• Hands-on experience with Tailscale at work or home
• Direct experience with Stripe or similar metered billing platforms (Metronome, Orb, OpenMeter)
• Experience building or scaling usage-based or consumption billing models
• Experience with cloud marketplace billing (AWS, GCP, Azure)
• Background in developer tools, infrastructure, or security-focused SaaS
• 0-to-1 product building experience — you've stood up a billing system or pricing model from scratch
• Familiarity with PLG/self-serve environments where billing is a core part of the user journey
• Experience with Salesforce CPQ or CRM ↔ billing system integrations
• Experience using LLMs and coding agents as part of your daily product workflows