Product Manager, Billing

Posted 4 weeks ago

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About the role

  • Senior Product Manager managing billing and monetization for Tailscale, focusing on entitlements and payment processes. Collaborating across Product and Engineering teams to optimize customer experience.

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.

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.

Job type

Full Time

Experience level

Mid levelSenior

Salary

CA$209,040 - CA$261,300 per year

Degree requirement

No Education Requirement

Tech skills

SQL

Location requirements

RemoteCanada

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