Staff/Lead Machine Learning Engineer, Behavior & Planning

The ML Observability team builds cutting-edge tools to monitor, explain, and improve AI systems in production, particularly those leveraging Large Language Models (LLMs) and generative AI. We provide robust, scalable observability for AI workloads, including drift detection and model evaluation, and behavior tracing, enabling customers to ship AI with confidence. As a Staff Engineer, you’ll lead the development of new features and foundational capabilities within Datadog’s LLM Observability product. You will shape product direction, drive experimentation, and apply your deep understanding of both AI systems and software engineering to solve open-ended problems in the fast-moving AI landscape. Your work will directly impact how our customers monitor, troubleshoot, and optimize LLM-based applications in production. Join us in building the foundational tools that make AI systems observable, understandable, and reliable in the real world. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do: Drive design and implementation of LLM observability features. Ideate, prototype, and scale new product features to provide insights and drive improvements for generative AI systems Work cross-functionally with other eng teams, product, UX, and applied science to iterate fast and find product-market fit Develop and extend tools for tracing, evaluating, and debugging LLMs Influence architecture decisions and mentor engineers to build resilient, high-performance systems Stay close to customer pain points and use those insights to guide product and engineering priorities Stay current with industry trends and advancements in machine learning and observability, driving innovation within the team Who You Are: You have a BS/MS/PhD in a Computer Science, Engineering or r

The Opportunity This is a critical and exciting time at Enigma. Our customers consistently tell us that our data products create tremendous value and are deeply aligned with their most important workflows. As demand grows, we have an urgent opportunity to improve both the intelligence of our data and the systems through which customers access it. We are looking for an experienced Senior/Staff Machine Learning Engineer to join our Match Team and help shape the next generation of Enigma’s customer-facing data products. In this role, you will combine advanced statistical and machine learning research with the engineering systems required to power fast, relevant, and reliable search experiences at scale. This is a uniquely high-impact role sitting at the intersection of information retrieval, ranking systems, semantic search, distributed systems, and customer data delivery. The Role At the core of Enigma’s product is our data, which makes both data science and delivery systems central to what we build. As a Senior/Staff ML Engineer on the Match Team, you will lead efforts that improve the relevance, latency, and scalability of our customer-facing data products. You’ll work across the full lifecycle: framing retrieval and ranking problems, developing models and experimentation strategies, evaluating results using real-world signals, and implementing high-throughput search and retrieval systems. This role is ideal for someone who is excited by both hard ranking/search problems and the systems challenges of turning those solutions into low-latency, production-grade retrieval systems. What You'll Do Develop innovative solutions to complex problems in information retrieval, ranking, semantic search, query understanding, and recommendation systems Build and optimize low-latency, high-throughput search APIs, indexing pipelines, and retrieval systems using Python, Typesense, and AWS Evaluate and evolve our search technology stack, driving technical design decisions across index

Airbnb was born in 2007 when two hosts welcomed three guests to their San Francisco home, and has since grown to over 5 million hosts who have welcomed over 2 billion guest arrivals in almost every country across the globe. Every day, hosts offer unique stays and experiences that make it possible for guests to connect with communities in a more authentic way. The Community You Will Join: AI and ML are at the heart of the Airbnb product. From Trust to Payments, and from Customer Service to Marketing, we rely on ML to ensure that guests and hosts have the best possible experience with Airbnb. The Core ML team is responsible for driving CSxAI (Customer Support x Artificial Intelligence) initiatives by adopting Generative AI technologies to enable an intelligent, scalable, and exceptional service experience. The team develops and enhances AI models, ML services, and tools including LLM fine-tuning and optimization, RAG/Search, LLM evaluation and testing automation, feedback-based learning, and guardrails for a wide range of applications at Airbnb. The richness of Airbnb's data, the complexity of its marketplace, and the variety innate in our product mean that we need to operate at the state of the art of AI practice. We are committed to long-term innovation to solve complex problems, and to do that we need experienced ML ​​The Difference You Will Make: In this Senior Staff role, you will set technical direction and lead execution for ML evaluation and the end-to-end data flywheel powering CSxAI products (e.g., assistive agents, issue resolution, and tooling). Your work will define how we measure quality, how we turn feedback into learning signals, and how we continuously improve models and products safely and efficiently. You will partner closely with product, engineering, design, operations to build evaluation systems that are trusted, scalable, and actionable - connecting offline metrics to online outcomes. A Typical Day: Define evaluation strategy and suc

We believe that the way people interact with their finances will drastically improve in the next few years. We’re dedicated to empowering this transformation by building the tools and experiences that thousands of developers use to create their own products. Plaid powers the tools millions of people rely on to live a healthier financial life. We work with thousands of companies like Venmo, SoFi, several of the Fortune 500, and many of the largest banks to make it easy for people to connect their financial accounts to the apps and services they want to use. Plaid’s network covers 12,000 financial institutions across the US, Canada, UK and Europe. Founded in 2013, the company is headquartered in San Francisco with offices in New York, Washington D.C., London and Amsterdam. We are the Data Foundation & AI team within Plaid’s Data organization. Our mission is to build the shared ML and AI infrastructure that powers intelligent capabilities across Plaid’s product suite. We develop the foundational systems, models, and data assets that transform Plaid’s unique financial network data into scalable, general-purpose representations that teams across the company can leverage. Our work spans the full ML lifecycle — from large-scale data curation and model pretraining to production serving, evaluation, and monitoring. As part of the team, you’ll work at the intersection of machine learning infrastructure, applied AI, and distributed systems, helping establish the core AI platform that enables innovation across Plaid. As a Staff Machine Learning Engineer, you will lead the technical strategy and development of Plaid’s foundation models, driving key decisions across pretraining objectives, model architecture, and fine-tuning approaches that power a wide range of downstream product applications. You will serve as the technical lead for the full machine learning lifecycle, overseeing everything from data curation and experimentation to production deployment, feature management,

About Taskrabbit: Taskrabbit is a marketplace platform that conveniently connects people with Taskers to handle everyday home to-do’s, such as furniture assembly, handyman work, moving help, and much more. At Taskrabbit, we want to transform lives one task at a time. As a company we celebrate innovation, inclusion and hard work. Our culture is collaborative, pragmatic, and fast-paced. We’re looking for talented, entrepreneurially minded and data-driven people who also have a passion for helping people do what they love. Together with IKEA, we’re creating more opportunities for people to earn a consistent, meaningful income on their own terms by building lasting relationships with clients in communities around the world. Taskrabbit is a hybrid company with employees distributed across the US and EU and a Built In — Best Places to Work (2022, 2023, 2024, 2025) continually ranked across multiple national and regional categories. Join us at Taskrabbit, where your work will be meaningful, your ideas valued, and your potential unleashed! This role is hybrid requiring 2 days in office at our San Francisco or NYC hub every Tuesday & Wednesday. About the Role Machine Learning is a cornerstone at Taskrabbit, and we're looking for a Staff Machine Learning Engineer to join our team and lead the next phase of our customer retention strategy. This is a critical, full-stack role for an individual who is passionate about the end-to-end lifecycle: from initial research and model development to building the robust systems that power repeat customer engagement and lifetime value growth at scale. Taskrabbit's greatest growth opportunity lies in deepening customer relationships and accelerating repeat purchases. Our most valuable customers are those who return frequently, discover new service categories, and increase their spending over time. There's significant untapped potential in the marketplace: repeat customers spend 3-5x more than one-time users, and category expan

About Taskrabbit: Taskrabbit is a marketplace platform that conveniently connects people with Taskers to handle everyday home to-do’s, such as furniture assembly, handyman work, moving help, and much more. At Taskrabbit, we want to transform lives one task at a time. As a company we celebrate innovation, inclusion and hard work. Our culture is collaborative, pragmatic, and fast-paced. We’re looking for talented, entrepreneurially minded and data-driven people who also have a passion for helping people do what they love. Together with IKEA, we’re creating more opportunities for people to earn a consistent, meaningful income on their own terms by building lasting relationships with clients in communities around the world. Taskrabbit is a hybrid company with employees distributed across the US and EU and a Built In — Best Places to Work (2022, 2023, 2024, 2025) continually ranked across multiple national and regional categories. Join us at Taskrabbit, where your work will be meaningful, your ideas valued, and your potential unleashed! This role is hybrid requiring 2 days in office at our San Francisco or NYC hub every Tuesday & Wednesday. About the Role Machine Learning is a cornerstone at Taskrabbit, and we're looking for a Staff Machine Learning Engineer to join our team and lead the next phase of our customer retention strategy. This is a critical, full-stack role for an individual who is passionate about the end-to-end lifecycle: from initial research and model development to building the robust systems that power repeat customer engagement and lifetime value growth at scale. Taskrabbit's greatest growth opportunity lies in deepening customer relationships and accelerating repeat purchases. Our most valuable customers are those who return frequently, discover new service categories, and increase their spending over time. There's significant untapped potential in the marketplace: repeat customers spend 3-5x more than one-time users, and category expan