Product Manager, Billing

<div class="content-intro"><p><strong>About Tailscale </strong></p> <p>Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.</p></div><p><span style="font-size: 12pt;"><strong>Job Description</strong></span></p> <p>We're looking for a Senior Product Manager to own Tailscale's billing and monetization infrastructure. You'll own the systems and experiences that power how Tailscale captures value: entitlements and plans, usage metering, payments, invoicing, and enterprise billing. This is the commercial backbone of Tailscale: every pricing model, every plan change, every invoice flows through your domain.</p> <p>You'll report directly to our VP Product, Ross Kukulinski, and collaborate with peers across Product, Engineering, Design, Finance, and Go-to-Market. You'll work closely with our Growth PM — they own the journey from signup through activation and conversion; you own the commercial infrastructure that makes those transactions work. </p> <p>This role requires real technical depth. You'll need to understand billing systems architecture well enough to partner with engineering on our Stripe integration, usage data ingestion APIs, entitlement enforcement, and payment processing — while also thinking strategically about pricing models, packaging, and how billing infrastructure enables or constrains business growth. You'll need to know Tailscale's product and customers well enough to design billing platform experiences that feel simple and transparent — even as the underlying complexity grows.</p> <p>Your initial focus will be on our core billing stack: plan and entitlement management, the payment and plan selection UX, and usage reporting and invoicing experiences. Over time, you'll expand into enterprise billing workflows — including Salesforce integration, custom entitlements, and cloud marketplace billing — and help build the scalable metering infrastructure that supports Tailscale's evolution toward usage-based pricing.</p> <p>We believe the billing experience should be as well-designed as the product itself. Usage reports should be clear. Invoices should be trustworthy. Plan selection should be effortless. You'll use data and product taste to build billing experiences worthy of a product our customers love.</p> <p><span style="font-size: 12pt;"><strong>Key Responsibilities</strong></span></p> <ul> <li>Own the product strategy and roadmap for Tailscale's entitlements, plans, and billing infrastructure</li> <li>Own the Stripe integration and payment processing stack — plan selection, payment UX, subscription lifecycle management</li> <li>Build and manage the usage data ingestion pipeline and APIs that power metering, usage reporting, and usage-based billing</li> <li>Design the UX for usage reports and invoices — making billing data clear and trustworthy for both self-serve and enterprise customers</li> <li>Define and manage entitlements and plan structures that map Tailscale's pricing and packaging to the features customers can access</li> <li>Own enterprise billing workflows, including Salesforce ↔ billing entitlement sync and custom enterprise plan management</li> <li>Partner with the Growth PM to build shared metering and event data infrastructure that serves both product analytics and billing</li> <li>Partner with Finance and GTM to develop and execute pricing and packaging changes, translating business strategy into product requirements</li> <li>Define and track key billing metrics (expansion revenue, billing-related churn, invoice accuracy, support ticket volume) and ... (truncated, view full listing at source)