Senior Software Engineer, AI Eval

Sentry • San Francisco, CA

1d • $240,000 - $280,000 • Hybrid

About The Position

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.

Requirements

• 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 (we use 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)

Nice To Haves

• experience evaluating LLMs, agentic systems, or AI-assisted developer tools

Responsibilities

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Number of Employees: 251-500 employees