Engineering Manager, Billing Products

About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the team The Billing team sits at the intersection of product, finance, and infrastructure. They're responsible for ensuring every observable event—errors, logs, traces, tokens—gets accurately measured, priced, and billed. Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns. The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models. As an Engineering Manager, you’ll lead a team of engineers owning critical workflows such as checkout and invoicing, while also developing new features to help customers manage their spend growth. In this role, you’ll partner across the organization to ensure our customers redeem everything Sentry has to offer and budget for future expansion. In this role you will Strategic Planning & Roadmap: Define and drive the team's roadmap. Align team goals with organizational objectives and contribute to the overall platform strategy. Technical Guidance & Operational Excellence: Provide technical leadership and guidance on complex distributed systems and design. Ensure the team is proactively identifying areas for improvement. Cross-functional Collaboration: Partner closely with business and technical teams to translate business goals into actionable objectives and scalable solutions. Team Leadership & Development: Lead, mentor, and grow a team of talented engineers, including Staff-level engineers. Build a culture of technical excellence, collaboration, continuous

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 Billing organization at Stripe builds and operates Stripe Billing, a growing product vertical inside of Stripe. Hundreds of thousands of businesses of all sizes and types use Stripe Billing to collect revenue for recurring and one-time payments across a variety of different pricing models—from selling SaaS subscriptions, to orchestrating multi-stage contracts, delivering business analytics, and providing recovery and retention tools to prevent customer churn. To support even the most unique and complex business models, our technology and products must be configurable and programmable. This requires our team to innovate in how we model different types of businesses, and how we use technology to enable customers to piece together Stripe’s Billing’s platform primitives into holistic solutions that support any type of business. Through this work, Stripe Billing allows worry-free innovation and evolution of any customer’s business model. Stripe is defining the industry’s approach to Billing solutions; we’re looking for innovators to join us. What you’ll do We’re looking for an experienced Engineering Manager to lead a team within the Stripe Billing organization. In this role, you will manage a high-performing team of engineers and partner closely with product managers and other cross-functional leaders to shape the team’s strategy and roadmap. You will excel in this role if you’re a product-focused engineering manager who can collaborate effe

About the Team The Applied organization brings OpenAI’s most advanced technology to the world through products like ChatGPT and the APIs that power a growing ecosystem of developer and enterprise applications. Data Engineering builds and operates the trustworthy, secure, and reliable data systems that power decisions across OpenAI. About the Role We’re looking for a Data Engineering Manager to lead the Growth & Revenue data engineering team. This leader will own the data strategy and execution for the data subject areas spanning growth accounting across all product surfaces, product partnerships, checkout, billing, payments, revenue, and monetization, helping OpenAI understand how people adopt, engage with, and pay for our products. You will partner closely with several Data Science, Business, and Engineering partners to connect product behavior to trustworthy subscriber, payment, and revenue measurement. In this role, you will: Build, manage, and grow a high-performing, inclusive team across the Growth & Revenue data subject areas. Define the data strategy for all the data subject areas you own. Deliver durable, well-modeled data products that connect product behavior, subscription state, checkout events, payment outcomes, and revenue. Establish trusted metric definitions and data quality standards so product, growth, finance, and executive leaders can make fast, consistent decisions. Partner with Data Science and Product teams to support experimentation, causal measurement, funnel analysis, and scalable self-serve analytics. Partner with Finance and Financial Engineering to ensure analytical revenue views reconcile to financial truth and production billing systems. Raise operational excellence for critical pipelines, including reliability, observability, privacy, governance, and incident response. Set a clear roadmap, make principled tradeoffs, and communicate progress and risk across technical and business stakeholders. You might thrive in this role if yo

About the Team The Premium team owns some of the highest-leverage customer-facing levers in ChatGPT’s consumer revenue business, spanning the paid customer journey: helping users understand the value of paid plans, convert with confidence, and continue finding lasting value in their subscription. Our work is highly cross-functional, partnering with Product, Data Science, Design, FinEng, Finance, Legal, Support, and Marketing to improve free-to-paid conversion, renewal, customer lifetime value, and revenue while keeping the experience trustworthy, scalable, and low-friction. In This Role, You Will: Lead and scale an engineering team responsible for some of ChatGPT’s most important subscription and monetization experiences. Own the technical execution for Premium customer experiences across plan merchandising, paywalls, upgrade flows, checkout UX, plan management, renewals, downgrades, and cancellation. Partner with Product and Data Science to run high-quality experiments across upgrade, trial, renewal, downgrade, and cancellation flows. Improve key subscription metrics including conversion, renewal, churn, ARPU, and lifetime value. Build reliable customer-facing Premium experiences for purchase, plan management, renewal, downgrade, cancellation, and access-related states at scale. Partner closely with FinEng and other platform teams to evolve the billing, payments, and entitlement capabilities that power Premium experiences. Collaborate closely with Product, Design, Data Science, Finance, Legal, Support, and Marketing on monetization strategy and execution. You Might Thrive in This Role If You: Have 5+ years of engineering management experience, Have strong technical expertise in backend, frontend, or full-stack development, with experience building growth-oriented features. Have a track record of improving conversion, retention, or monetization through experimentation and data-driven product engineering. Are experienced with subscription products, plan merchandising

About the Team Our team turns OpenAI’s latest model capabilities into polished, trusted products for consumers and developers. We build the end-to-end experiences including product surfaces, platform layers, and developer workflows that make cutting-edge AI accessible, useful, and dependable at scale. OpenAI’s Financial Engineering (FinEng) team powers how revenue flows through our products - pricing and packaging, checkout, payments, subscriptions, and the financial infrastructure behind them. We partner closely with Engineering, Data Science, Risk, Finance, and Go-to-Market to make paying for OpenAI products seamless, reliable, and efficient worldwide. We pair rapid innovation with a rigorous approach to responsible deployment. Safety and trust are built into how we design, ship, and learn from real-world usage, so these tools deliver meaningful value while aligning with OpenAI’s mission. About the Role We are seeking an experienced Product Manager to scale the product efforts and technical strategy within our Financial Engineering team. The ideal candidate has prior experience in billing, finance, and accounting, ideally also building solutions for commercial users of varying sizes from small scale to enterprise. This role requires close collaboration with our product, finance, operations, and engineering teams. This position is based in San Francisco, CA. We utilize a hybrid work model with 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Develop a strategy and roadmap to efficiently scale the billing operations and customer experience behind OpenAI’s growing product portfolio Identify and execute opportunities to improve the order-to-cash processing for OpenAI’s largest and most strategic customers Build AI powered tooling for key partner teams such as Finance and User Operations to drive better decisions and business outcomes Collaborate with other product teams to defining OpenAI’s evolving monetization s

About the Team OpenAI Finance ensures the organization is positioned for long-term success as we pursue our mission. The Order to Cash (OTC) team oversees the complete flow of commercial transactions from order intake and provisioning through billing, collections, and cash application — ensuring accuracy, compliance, and operational excellence in support of OpenAI’s mission to ensure artificial general intelligence benefits all of humanity. About the Role We are seeking a Senior Manager to build and scale Order to Cash across OpenAI’s API and ChatGPT businesses, cloud marketplaces, and strategic partnership channels. This role will own end-to-end Order Management and Billing operations across API and ChatGPT while leading OTC readiness and execution for AWS Marketplace, Google Cloud Marketplace, Oracle Cloud Marketplace, GovCloud, and future partner channels. The role will also own the end-to-end Order Management and Billing close, setting the close calendar, readiness standards, review and sign-off expectations, while leading the team responsible for execution. You will oversee the Order Management and Billing lifecycle across API, ChatGPT, marketplace, and partner transactions, spanning commercial readiness, order intake, provisioning, usage and transaction data, pricing validation, invoicing, credits, settlements, and product and partner reporting. Your work will ensure transactions are accurate, timely, complete, and supported by audit-ready controls. This is a leadership role that combines strategic ownership, cross-functional leadership, and hands-on operational execution. You will define the target operating model, lead first-of-kind launches, shape product and systems roadmaps, and oversee the resolution of complex contract modifications, non-standard pricing, usage disputes, reconciliation breaks, settlement variances, and customer- or partner-impacting escalations. You will collaborate with teams across Finance, GTM, Product, Engineering, Legal, Tax, Reven