Senior Software Engineer, AI Evals

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...