Senior Product Manager owning provider experience and clinical operations products at Maple, Canada’s on - demand healthcare platform. Driving scalable workflows and AI - enabled care delivery improvements.
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.
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