Partner Applied AI Engineer

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 As a Senior Software Engineer on Sentry’s AI/ML team, you’ll be responsible for building the evaluation infrastructure that measures the accuracy, reliability, and real-world performance of our AI systems. This role is critical to ensuring that our debugging agents and AI-powered features behave correctly, safely, and predictably as they scale. You’ll design datasets, benchmarks, and test harnesses that turn ambiguous AI behavior into measurable signals, helping the team ship AI with confidence. In this role you will Design and build robust evaluation frameworks to measure accuracy, reliability, regressions, and edge cases in AI systems Create and curate high-quality datasets, golden test cases, and benchmarks grounded in real production data Build automated test harnesses and metrics pipelines to continuously evaluate models, prompts, and agentic workflows Partner closely with applied AI engineers and product leaders to define what “good” looks like and translate it into measurable criteria Own the evaluation lifecycle for major AI initiatives, from early experimentation through production monitoring You’ll love this job if you Care deeply about correctness, rigor, and measurement in AI systems Enjoy turning fuzzy product goals and model behavior into concrete tests and metrics Like building foundational infrastructure that unlocks faster iteration and higher confidence for the entire AI team Thrive in cross-functional environments and enjoy influencing model design through better evaluation Qualifications Minimum 5+ years of professional experience with a Bachelor’s degree in computer science, machine learni

About the Team GTM Growth Engineering builds AI-native products that help OpenAI's go-to-market and B2B marketing organizations scale with greater speed, intelligence, and operational effectiveness. We apply OpenAI models to real business workflows and build the systems that make those applications useful and dependable: customer context, agent behavior, feedback, evaluation, experimentation, and appropriate human oversight. Our work brings together software engineering, applied AI, product, data, and GTM operations. We measure success through the quality of customer engagement, pipeline, conversion, and the effectiveness of our sales and marketing teams. About the Role We're looking for an Applied AI Engineer to build production systems that help AI-powered go-to-market workflows improve over time. You will connect agent behavior, customer and operator feedback, evaluation, experimentation, and business outcomes to make these systems more effective, reliable, and responsive to evolving customer needs. This is a deeply technical, cross-functional role with end-to-end ownership of the agent improvement loop: understand production behavior, identify failure modes, improve how the system decides or acts, and validate the resulting impact. You will partner with Engineering, Product, Data Science, Sales, and B2B Marketing to turn real-world signals into safer, more effective agent behavior and measurable improvements in customer engagement, conversion, qualified pipeline, and team productivity. In this role, you will: Own the production improvement loop across agent behavior, customer and operator feedback, evaluation, experimentation, and verified business outcomes. Instrument agent workflows so model interactions, tool use, decisions, failures, human edits, and downstream outcomes can be understood in context. Define meaningful quality standards, representative evaluation datasets, regression coverage, and production monitoring for real GTM workflows. Investigate why a

About the team The Applied AI Engineering team is responsible for ensuring the safe and effective deployment of Generative AI applications for developers and startups. We act as a trusted advisor and thought partner for our customers, working to build an effective backlog of GenAI use cases for their industry and drive them to production through strong technical guidance. OpenAI's customers represent a range of diverse backgrounds and maturity, from early-stage startups to late-stage startups. About the Role We are seeking a technically proficient, business-minded Applied AI Engineer to help push the frontier of advanced AI with our strategic startup customers. You'll work with some of the most exciting AI startups in the world, guiding them through ideation, development, delivery, and scaling to accelerate and maximize the value of what they build on our platform. You will have the opportunity to work on the most novel and creative use cases being built on our API, serving as a critical partner in collecting and delivering high-fidelity product and model feedback internally. You will collaborate closely with Sales, Solutions Engineering, Applied Research, and Product teams, and you will report to the Startups Applied AI Lead. This role is based in our San Francisco or New York offices. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Partner closely with strategic startup customers as their technical thought partner to build novel applications on our API, helping them rapidly move from ideation to scale. Provide proactive guidance to maximize business impact and accelerate application development. Experiment and prototype alongside customers, demonstrating practical use cases. Contribute to open-source resources and scale the function by sharing knowledge, codifying best practices, and publishing useful resources. Synthesize and deliver valuable feedback to the Product and Research

About the team The Applied AI Engineering team is responsible for ensuring the safe and effective deployment of generative AI applications for developers and enterprises. We act as a trusted advisor and thought partner for our API customers, working to build an effective backlog of frontier AI use cases for their industry and drive them to production through strong technical guidance. As an Applied AI Engineer in the Digital Native segment, you’ll work with industry-leading technology companies like Stripe, Uber, and Reddit to bring new AI capabilities into the products their customers use every day. You’ll partner directly with experienced product and engineering teams to turn frontier model capabilities into new features and agentic experiences. The work combines rapid experimentation with the demands of established products: complex systems, real users, and high expectations for quality and performance. Lessons from these deployments inform OpenAI’s product and research teams. About the role You will combine deep technical judgment, hands-on engineering, and customer leadership to take ambitious ideas from use-case selection and architecture through prototyping, evaluation, production launch, and scale. You will write and debug code, build evaluation systems, resolve complex integrations, and guide decisions involving model behavior, reliability, latency, cost, safety, security, governance, and operational readiness. Success is measured by production systems, sustained adoption, and meaningful customer impact – not simply activity or successful demonstrations. This is a rare opportunity to work on consequential real-world deployments at the frontier of AI while directly influencing how OpenAI’s products evolve. This role is based in our SF or Seattle office. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Deeply embed with our most sophisticated and technical platform customers,

About the team The Applied AI Engineer - Digital Natives team is responsible for ensuring the safe and effective deployment of Generative AI applications for developers and enterprises. We act as a trusted advisor and thought partner for our customers, working to build an effective backlog of frontier AI use cases for their industry and drive them to production through strong technical guidance. As an Applied AI Engineer in the Digital Native segment, you’ll help large and highly sophisticated companies transform their business through custom AI solutions applications such as customer service, automated content generation, contextual search, personalization, and other novel use cases leveraging OpenAI’s newest, most exciting models and latest capabilities. About the role We are looking for a driven solutions leader with a product mindset to partner with our customers and ensure they achieve tangible business value with frontier AI. You will pair with senior customer leaders to establish AI strategic roadmaps and identify the highest value applications. You’ll then partner with their engineering and product teams to move from prototype through production. You’ll take a holistic view of their needs and design an enterprise architecture using OpenAI APIs and other services to maximize customer value. You will collaborate closely with Sales, Solutions Engineering, Applied Research, and Product. This role is based in our SF or Seattle office. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Deeply embedded with our most sophisticated and technical platform customers, serving as their technical thought partner in ideating and building novel applications on our APIs. Proactively provide guidance to our customers on how to maximize business impact from their applications, accelerating their time to value. Experiment and prototype solutions with and for your customers. Forge and manage relat

About the team The Technical Success team is responsible for ensuring the safe and effective deployment of ChatGPT and OpenAI API applications for developers and enterprises. We act as a trusted advisor and thought partner for our customers, ensuring developers and enterprises maximize value from our models and products. The Ecosystem team builds and scales third-party integrations around ChatGPT and Codex. We work across product, engineering, partnerships, safety, legal, policy, and go-to-market to create integrations that are useful, trustworthy, and technically sound. About the role We’re looking for an Applied Deployment Engineer to help build and deepen ChatGPT integrations with third-party messaging platforms. The initial focus will be on partner work as well as future opportunities with other messaging apps around the world. This is a hands-on, partner-facing engineering role. You’ll work closely with external product and engineering teams to improve existing integrations, expand capabilities such as image generation, increase retention, and translate partner needs back into OpenAI’s product and engineering roadmap. You should be comfortable writing code daily, making changes across platform or monorepo surfaces when needed, and moving fluidly between technical discovery, product tradeoffs, prototyping, debugging, and executive-level communication. This role is best suited for a strong product-minded engineer with excellent communication skills, sound technical judgment, and the ability to work across cultures, time zones, and organizations. This role is based in our San Francisco office. We use a hybrid work model of 3 days in the office per week and offer relocation assistance to new employees. In this role, you will: Partner with messenger app product and engineering teams to design ChatGPT-powered experiences that fit naturally into chat, group, contact, and app-tab surfaces. Deepen existing partner integrations, with an initial focus on improving user ex