Staff Software Engineer, Stripe Scale & Bundles

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The Packaging team within User Billing is responsible for Stripe Scale — Stripe's flagship product bundle that brings together Payments, Radar, Tax, and other Stripe products into a unified, tiered pricing offering for self-serve and sales-assisted users. A core part of our approach is using Stripe's own Billing product to power how we charge for Stripe itself — essentially making Stripe our own most demanding customer. This "dogfooding" strategy means we integrate our external-facing subscription, usage-based billing, and entitlement products into our internal monetization stack, generating real-world insights that directly improve our products for enterprise customers with complex billing needs. This is a uniquely cross-functional domain. Stripe Scale sits at the intersection of pricing strategy, subscription management, entitlements, usage-based billing, fee calculation, and settlement — spanning both Stripe's internal commerce platform and Stripe's external Billing product. The Packaging team partners closely with Product, Sales, Finance, Accounting, Connect, Tax, Revenue Recognition, and many product engineering teams across Stripe to define, price, and operationalize bundles. As the team grows beyond Stripe Scale into additional bundle offerings, we need a technical leader who can not only design and build complex distributed systems, but also navigate the organizational complexity of delivering a product that touches nearly every corner of Stripe. What you'll do We're looking for a Staff Engineer who combines deep technical skill with exceptional relationship-building and communication abilities. You will be the connective tissue between the Packaging team and its many stakeholders, driving alignment across engineering, product, and business functions while ensuring sound technical execution. You will: Drive cross-team technical strategy and alignment for Stripe Scale and future bundles, working across Stripe's internal commerce platform, Stripe Billing, Connect, Tax, Revenue Recognition, Accounting, and Finance to ensure cohesive system design and delivery Be the primary technical point of contact for partner teams, proactively building relationships, establishing shared context, and creating clarity on dependencies, timelines, and tradeoffs Lead the design of complex, multi-system integrations — we use Stripe's own Billing product to bill for Stripe, which means you'll architect systems spanning subscription orchestration, billing routing, usage tracking, entitlement management, fee settlement, and invoice generation across both internal and external billing platforms Translate ambiguous business requirements into clear technical plans, working closely with Product and business stakeholders to identify the right technical approach for evolving packaging and pricing strategies (e.g., new tiers, bundle versioning, sales-sold transitions) Drive decision-making through influence, not authority, bringing engineering leaders and cross-functional partners together to resolve competing priorities, negotiate resource commitments, and align on roadmaps — especially in areas where the Packaging team depends on other teams' delivery Ensure operational excellence by establishing strong patterns for testing, incident response, and billing accuracy across the dual-system architecture (internal commerce platform + Stripe Billing) — where misbillings directly impact Stripe's revenue and user tru ... (truncated, view full listing at source)