TL;DR

Product Manager (SaaS Billing): Own and develop Tailscale's billing and monetization infrastructure including entitlements, usage metering, payments, invoicing, and enterprise billing. With an accent on billing systems architecture, pricing models, and usage-based billing. Focus on designing clear billing experiences, managing Stripe integration, and enabling scalable commercial infrastructure.

Location: Remote within the United States only

Salary: $156,000 - $195,000 USD

Company

Tailscale builds software to securely interconnect people and devices globally, focusing on ease, security, and scalability in networking.

What you will do

  • Own product strategy and roadmap for billing infrastructure including entitlements and plans.
  • Manage Stripe integration and payment processing stack.
  • Build and maintain usage data ingestion pipelines and APIs for metering and billing.
  • Design UX for usage reports and invoices for self-serve and enterprise customers.
  • Manage enterprise billing workflows including Salesforce integration and custom plans.
  • Collaborate cross-functionally with product, engineering, finance, and go-to-market teams.

Requirements

  • Must have 4+ years in product roles owning billing, payments, or monetization systems at SaaS or tech companies
  • Strong understanding of billing systems architecture and subscription lifecycle management
  • Experience with pricing and packaging strategy and cross-functional coordination
  • Proficiency with data analytics tools like SQL, Looker, Snowflake
  • Ability to explain complex billing concepts to technical and non-technical stakeholders
  • Must be located in the United States (remote within US only)

Nice to have

  • Experience with Stripe or similar metered billing platforms
  • Experience building usage-based billing models and cloud marketplace billing
  • Background in developer tools, infrastructure, or security SaaS
  • Experience with Salesforce CPQ or CRM-billing integrations
  • Experience using LLMs and coding agents in product workflows

Culture & Benefits

  • Inclusive, flexible remote-first environment supporting authentic self-expression
  • Competitive compensation including base salary, equity, and benefits
  • Comprehensive health, vision, dental coverage with no waiting period
  • Home office setup budget and monthly internet reimbursement
  • Generous paid time off and parental leave from day one
  • Professional development budget and mentorship opportunities