Staff Software Engineer, Stripe Scale & Bundles

Stripe

About The Position

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. 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.

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

Nice To Haves

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

Responsibilities

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

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