Engineering Manager, Billing Platform

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 role Sentry is looking for an Engineering Manager to lead our Growth team (internally called "Value Discovery") and help expand our product-led business by helping customers discover and get the most out of our platform. At Sentry, we do growth with an explicit bias for customer value. Our experiments are rooted in strong product sense and empathy for developers, not conversion pressure. We never surprise developers with new charges or push features they don't need. In a binary tradeoff between doing good by the customer or good by the business, the customer always wins. You'll collaborate closely with several areas of the business including Product, BizOps, Data, Design, and GTM to identify the moments in a developer's workflow where Sentry can deliver more value, make that value easier to find, and support that your approach works with data. In this role you will You'll lead a team of engineers, set its priorities, and be accountable for the metrics it moves. This is a new role, and the roadmap is yours to define and execute in partnership with design and data teams. Lead work across Sentry's self-serve funnel — signup and onboarding, first-run activation moments in-product, trial and upgrade paths, and pricing and billing surfaces in partnership with the Billing team — largely in our Python/Django and TypeScript/React codebase Evolve our experimentation foundations, in close partnership with our Data team — flagging, instrumentation, and readouts are real but far from finished Run a fast, disciplined experimentation loop where hypotheses are argued before they're built Hold conversion and activation alongside ch

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

Why join us Brex is the intelligent finance platform that enables companies to spend smarter and move faster in more than 200 markets. By combining global corporate cards and banking with intuitive spend management, bill pay, and travel software, Brex enables founders and finance teams to accelerate operations, gain real-time visibility, and control spend effortlessly. Brex’s AI-native automation and world-class service eliminate manual expense and accounting tasks for customers so they can focus on what matters most. Tens of thousands of the world's best companies run on Brex, including DoorDash, Coinbase, Robinhood, Zoom, Plaid, Reddit, and SeatGeek. Working at Brex allows you to push your limits, challenge the status quo, and collaborate with some of the brightest minds in the industry. We’re committed to building a diverse team and inclusive culture and believe your potential should only be limited by how big you can dream. We make this a reality by empowering you with the tools, resources, and support you need to grow your career. Operations Operations is the backbone of Brex’s mission to power businesses through our Intelligent Finance Platform. We own credit, fraud, money movement, and payments, protecting our customers and our company. From product operations that ensure flawless launches to scalable systems that drive innovation and precision, we operate at the intersection of product, design, engineering, and customer success. If you want to work at the heart of the business, Operations is where you belong. What You’ll Do Account Servicing owns what happens to a Brex account after it's live: money applied against statement balances, billing terms changed, auto-pay kept working, points debited and granted, credit performance reported to the bureaus, and accounts closed cleanly. We're hiring a manager to run that portfolio. You'll inherit a team with deep subject-matter expertise in specific queues, a set of in-flight migrations from other teams, and a

ABOUT BASETEN Baseten powers mission-critical inference for the world's most dynamic AI companies, like Cursor, Notion, OpenEvidence, Abridge, Clay, Gamma and Writer. By uniting applied AI research, flexible infrastructure, and seamless developer tooling, we enable companies operating at the frontier of AI to bring cutting-edge models into production. We're growing quickly and recently raised our $1.5B Series F , led by Altimeter Capital, Conviction Partners, and Spark Capital. Join us and help build the platform engineers turn to to ship AI products. PRODUCT AT BASETEN Product at Baseten is a nascent function. Our company today has a strong engineering culture, is heavily customer-obsessed, and moves fast. We're building the product function now, and you'd be one of the people who defines it. You'll work directly with our founders and with some of the best systems and infrastructure engineers in the world, and you'll set the standard for what product looks like here. You earn trust by being technical, finding the truth in front of customers, building great cross-functional relationships, and shipping great product experiences. THE ROLE The largest, most demanding Enterprises are starting to run on Baseten and they come with a range of security, compliance, and procurement requirements. Today that readiness is assembled deal-by-deal. You'll own the enterprise-readiness surface end to end and turn it into product: the deployment options customers can choose and buy, compliance posture they can trust, access and security controls their IT teams require, and the billing and spend controls their finance teams expect. What does a complete Baseten Enterprise Product offering look like? RESPONSIBILITIES Drive the Enterprise Readiness customer experience end to end: Partner with GTM and Enterprise Engineering to make "enterprise-ready" a platform-wide capability, not a deal-by-deal scramble. Outcome: readiness becomes a supported, priced product instead of bespoke work asse

ABOUT BASETEN Baseten powers mission-critical inference for the world's most dynamic AI companies, like Cursor, Notion, OpenEvidence, Abridge, Clay, Gamma and Writer. By uniting applied AI research, flexible infrastructure, and seamless developer tooling, we enable companies operating at the frontier of AI to bring cutting-edge models into production. We're growing quickly and recently raised our $1.5B Series F , led by Altimeter Capital, Conviction Partners, and Spark Capital. Join us and help build the platform engineers turn to to ship AI products. THE ROLE The largest, most demanding enterprises are starting to run on Baseten, and they arrive with a range of security, compliance, and procurement requirements. As a Senior Engineer on Baseten's enterprise engineering team, you'll build the capabilities that enable large organizations like Writer, HubSpot, and Notion to succeed on Baseten. Enterprise engineering authors the core building blocks, APIs, and user experiences powering the Baseten platform: identity and access management, billing, regional isolation, and self-hosted and single-tenant deployment options. This is deep product and systems work across the full stack, from designing authentication and authorization systems using standards like OAuth and OIDC to shipping the admin experiences enterprise IT teams use to manage their organization. EXAMPLE INITIATIVES Recent and upcoming work on the team: Fine-grained authorization for users, service accounts, and agentic workloads SSO and SCIM support, allowing customers to centralize and automate access to Baseten Expanding the billing platform to support evolving pricing models, advanced data exports, and controls to manage spend In-product management and enforcement of customer compliance requirements like data residency and HIPAA Securing network paths in and out of a customer's models with private connectivity and ingress and egress restrictions Allowing customers to run Baseten inside their own VPC, on-pr