Product Manager, Billing

About Tailscale 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. Job Description 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. 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. 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. 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. 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. Key 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 What We Are Looking For 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 Nice to Have Hands-on experience with Tailscale at work or home Direct experience with Stripe or similar metered billing platforms (Metronome, Orb, OpenMeter) Experience building or scaling usage-based or consumption billing models Experience with cloud marketplace billing (AWS, GCP, Azure) Background in developer tools, infrastructure, or security-focused SaaS 0-to-1 product building experience — you've stood up a billing system or pricing model from scratch Familiarity with PLG/self-serve environments where billing is a core part of the user journey Experience with Salesforce CPQ or CRM ↔ billing system integrations Experience using LLMs and coding agents as part of your daily product workflows As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set. CAN Pay Ranges $209,040—$261,300 CAD Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life. A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family! Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description. Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration. Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.