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.

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 trust

• Mentor and uplevel engineers on the team, with a particular emphasis on cross-team collaboration skills, stakeholder management, and writing clear technical proposals and decision documents
• Communicate transparently and proactively to leadership and partner teams — surfacing risks early, framing tradeoffs clearly, and building trust through consistent follow-through
• Own and evolve the technical roadmap for the Packaging domain, balancing near-term delivery (Stripe Scale GA and beyond) with long-term platform investments for future bundles
• Drive interoperability across Stripe's internal commerce platform, Stripe Billing, and the broader product ecosystem — ensuring that pricing, subscriptions, entitlements, usage, fee calculation, settlement, and reporting work cohesively

Lead cross-team and cross-org technical efforts, including the complex integration between Stripe's internal commerce platform and Stripe Billing — spanning billing router design, event transformation pipelines, and usage/entitlement tracking systems

• Partner with Product to shape packaging strategy from a technical feasibility lens — including bundle composition, tiering, upgrade/downgrade flows, and eligibility logic
• Build and maintain strong working relationships with engineering leads on partner teams (Billing V2, Connect, Tax, Revenue Recognition, Accounting Automation) to ensure aligned priorities and smooth execution
• Represent the Packaging team's technical needs in planning forums, execution reviews, and cross-org discussions — advocating clearly and constructively for the team's dependencies
• Establish engineering best practices for the team including design review processes, testing strategies for multi-system billing flows, and incident remediation playbooks
• Contribute hands-on to critical system design and implementation, particularly in areas requiring deep understanding of both the internal commerce platform and Stripe Billing APIs
• Who you are
• Minimum requirements
• 10+ years of professional software development experience, including technical leadership of projects spanning multiple teams or product areas
• Demonstrated excellence in cross-team collaboration and stakeholder management — you have a track record of building strong relationships across engineering, product, and business functions to drive complex, multi-team initiatives to completion
• Exceptional communication skills — you can distill complex technical concepts for diverse audiences, write clear and persuasive design documents, and facilitate productive discussions that lead to decisions
• Experience navigating organizational complexity — you've successfully led technical efforts where success depended not just on your team's execution, but on influencing and aligning with teams you don't directly control
• Strong systems design experience, particularly in architecting large-scale distributed systems involving event-driven architectures, data pipelines, or billing/financial systems
• Experience influencing company or org strategy at the intersection of business needs and technology — you measure your success in terms of business outcomes and team effectiveness, not just technical elegance
• A collaborative leadership style — you lead through influence, earn trust through reliability, and create an environment where teams across org boundaries want to work with you
• Demonstrated ability to mentor and invest in the development of engineers, with particular strength in coaching others on cross-functional effectiveness
• Preferred qualifications
• Prior experience in financial technology, particularly in billing systems, payment processing, pricing/packaging, or revenue operations
• Experience with internal dogfooding architectures — where you've used your own company's products to power internal operations and driven improvements from the inside out
• Experience building or evolving subscription management, usage-based billing, or entitlement systems
• Familiarity with the challenges of operating dual billing systems or migrating billing infrastructure between platforms

Experience working in environments where multiple teams must co-deliver a single user-facing product