Engineering Manager, Customer Trust

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

Join us in building the future of finance. Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading. About the team + role The Credit Cards & Banking team is part of Robinhood’s Money Engineering organization. This team builds the products and systems behind some of Robinhood’s most ambitious consumer experiences, including Robinhood Gold Credit Card, Banking, and the next generation of card and banking products. This is a high-impact engineering leadership role at the intersection of product innovation, scale, and reliability. Our team owns the full customer experience end to end—from mobile and frontend surfaces to backend systems and the infrastructure that powers them. We work on products used by millions, in a space where execution quality, technical rigor, and customer trust matter deeply. As an Engineering Manager, you’ll lead a team of engineers building category-defining credit card and banking experiences. You’ll partner closely with product, design, data, compliance, operations, and peer engineering teams to define the roadmap, make sound technical decisions, and deliver exceptional products at scale. You’ll also play a central role in hiring, coaching, and developing a high-performing team. We’re looking for bold thinkers, sharp problem-solvers, and leaders who want to help build the future of money. This role is based in our Menlo Park, CA or New York, NY office(s), with in-person attendance expected 5 days per week. At Robinhood, we believe in the power of in-person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high-performing teams. What you’ll do Lead, grow, and support a team of software engineers workin

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 us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. What you’ll do Lead the design and delivery of production-grade AI agents : We believe the best managers lead from being hands-on and close to the work. Our managers operate as ICs for their first 3-6 months at Sierra, and then evolve to manage and grow a team of engineers, all while building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact. Own the Agent Development Life Cycle (ADLC): You’ll both build directly, and guide your team through the ful

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 us Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor and Clay Bavor . Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. What you'll do Scale The Function: Lead, coach, and develop a high-caliber SE team, providing guidance, assigning projects and ensuring technical excellence. Conduct regular performance evaluations, foster professional growth, and coach team members to reach their full potential. Player-Coach: Be a true player-coach who stays in the work: own your own enterprise deals as an individual contributor, running discovery, demos, and technical deep dives alongside your team, while leading and growing a team of high-growth enterprise SEs. Set the bar by example, jump into the most strategic cycles, and turn what you learn in the field into coaching and playbooks that raise the whole team. As the team grows, become a strategic leader and more manager focused. GTM Te