Product Manager, Billing at Tailscale

This role is ideal for a technically-minded Senior Product Manager with a deep background in monetization and billing infrastructure at scale. You’ll need 4+ years of experience managing complex systems like usage-based metering, Stripe integrations, and entitlement engines. Because this product is engineer-focused, you should be comfortable engaging in high-level architectural discussions with engineers while balancing the strategic needs of finance and GTM teams. The compensation is highly competitive ($209k – $261k CAD) for a fully remote position in Canada. Tailscale offers a robust "remote-first" culture with premium perks, including a $1,000 home office stipend, $1,500 for professional development, and up to 26 weeks of parental leave top-ups. You will report directly to the VP of Product, giving you high visibility and the opportunity to build the commercial "backbone" of a rapidly growing network security company. **You might be a good fit if you...** * Have hands-on experience scaling usage-based or consumption billing models in a SaaS environment. * Are proficient with data tools like SQL, Snowflake, or Looker to analyze revenue and usage data. * Believe that billing UX (invoices and usage reports) should be as polished and user-friendly as the core product. * Can navigate the complexities of both PLG self-serve flows and enterprise-grade Salesforce/CPQ integrations.