Engineering Manager, Billing

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

We are a Canadian leader in digital automotive solutions. Our flagship brands — AutoTrader.ca , AutoSync , Dealertrack Canada and CMS — help Canadians buy, sell, and finance vehicles with confidence. AutoTrader.ca is Canada’s largest automotive marketplace, with over 25 million monthly visits . Through AutoSync , we provide software solutions to 3,500+ dealers , streamlining their operations, marketing, and sales. Dealertrack Canada is the country’s top automotive financing portal, processing more than 6.5 million credit applications each year. Collateral Management (CMS ) is a national tech solution that boosts lien and registration services , recovery services , and insolvency management solutions for Canadian Lenders As part of AutoScout24 group , Europe’s largest online car marketplace, we’re shaping the future of automotive retail in Canada and beyond. Join us on our journey as we bring together the best of Europe and North America to shape the future of automotive retail. --- We are seeking a highly experienced Engineering Manager to lead the strategy, design, delivery, and operational excellence of integrations, automations, and enterprise platform initiatives across ERP, Billing, Revenue, CRM, HRIS systems. This role requires a strong technical and people leader with deep expertise in enterprise systems, data flows, platform modernization, migration programs, and large-scale delivery execution. Key Responsibilities: Lead the design and delivery of enterprise integrations and automation solutions across ERP, Billing, Revenue, CRM, HRIS, and related platforms. Define scalable integration patterns, system interfaces, API strategies, data flows, and engineering standards across enterprise applications. Apply an AI-first approach to solution development by identifying opportunities to improve automation, operational efficiency, insights, and engineering productivity through AI-enabled capabilities where

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 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