ML Engineer - Automated Evaluation and Adversarial Design

Day-to-day work involves designing, building, and maintaining automated evaluation systems that assess AI feature quality at scale, including multi-turn conversation evaluation and end-to-end agent workflow testing. This includes creating adversarial test suites that probe model weaknesses and running stress tests to ensure features perform under demanding conditions, with particular focus on failure modes that only emerge across extended interactions, such as: context degradation, goal drift, and compounding errors. Typical deliverables include: evaluation frameworks and rubrics, quality assessment reports, adversarial test case libraries, multi-turn stress-test pipelines, and recommendations on model readiness. Define and own the automated evaluation approach for AI features, translating qualitative notions of quality into measurable, reproducible assessments across both single-turn and multi-turn agentic experiences Build adversarial test suites that target known and emerging model failure modes, including edge cases relevant to productivity application workflows including conversation-level failures such as context loss, instruction forgetting, and cascading errors across multi-step tasks Develop and execute stress test protocols that validate minimum performance thresholds under atypical input conditions including extended conversation lengths, adversarial mid-conversation topic shifts, and complex tool-use sequences Ensure alignment between automated and human evaluation methods on an ongoing basis, identifying and resolving systematic disagreements Collaborate with engineering partners to integrate evaluation into development and release workflows Scale adversarial test case generation and stress test execution, leveraging automation where appropriate, including programmatic generation of multi-turn conversation scenarios and agent interaction traces Influence model and feature quality decisions by communicating evaluation findings and readiness assessments to cross-functional partners Bachelor’s degree in Computer Science, Machine Learning, Statistics, or a related field 4+ years of experience building or significantly extending ML evaluation systems, including designing evaluation benchmarks or quality assessment frameworks including evaluation of sequential or multi-step AI outputs Experience independently defining evaluation architecture and methodology for AI or ML systems with the ability to design evaluation approaches where the unit of analysis is a conversation or session rather than a single output Experience designing adversarial or red-teaming test methodologies for ML models or AI-powered features including adversarial scenarios that target failures across multi-turn interactions Experience with Python and ML frameworks (PyTorch, TensorFlow, or equivalent) in production or near-production settings Track record of owning technical direction for evaluation efforts across multiple features or product areas Experience evaluating user-facing AI features in consumer applications, with an understanding of how technical metrics connect to user-perceived quality Familiarity with productivity software or creative tools, with the ability to assess output quality from a user workflow perspective Experience ensuring alignment between automated and human evaluation methods, including inter-annotator agreement analysis and bias detection Track record of designing evaluation systems that scale across multiple features or product areas without requiring bespoke solutions for each Experience evaluating different types of AI systems, including API-based and custom-trained models Demonstrated ability to communicate evaluation findings and readiness assessments to cross-functional partners Experience leveraging automation to scale evaluation data generation and analysis Experience building evaluation pipelines for conversational AI, dialogue systems, or agentic workflows, including turn-level and session-level automated scoring Familiarity with agent orchestration frameworks (LangChain, LangGraph, CrewAI, AutoGen) and observability tooling (LangSmith, Braintrust, Arize), with an understanding of how to instrument and evaluate multi-step agent runs Experience designing adversarial tests for tool-use reliability, function-calling accuracy, or agent planning quality Graduate degree in a relevant field

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