Senior Software Engineer, AI Evals
Build evaluation infrastructure for AI systems at Sentry, designing datasets, benchmarks, and test harnesses to measure accuracy and reliability of debugging agents. Requires 5+ years experience, Python/TypeScript proficiency, and AI/ML background.
About the job
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 learning, or a related field
- Experience building testing, evaluation, or data infrastructure for complex systems (AI/ML experience strongly preferred)
- Comfort writing production-quality code (Python and TypeScript)
- Experience working with structured and unstructured datasets, labeling workflows, or data quality pipelines
- Familiarity with modern ML systems and evaluation techniques (e.g., offline metrics, online evaluation, regression testing for models or prompts)
- Bonus: experience evaluating LLMs, agentic systems, or AI-assisted developer tools
Base salary range: $240,000 to $280,000 USD.
Skills
Python, TypeScript, Machine Learning, Ai Evaluation, LLMs, Datasets, Metrics Pipelines, Evaluation Frameworks, Agentic Systems, Data Infrastructure
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