About the Role As a Member of Technical Staff - Evals at Entendre, you will play a key role in ensuring the quality and reliability of our AI-powered features. Your primary responsibilities will include: • Designing and maintaining evaluation frameworks to measure the accuracy, reliability, and regression behavior of our AI capabilities. • Building automated test harnesses that operate on real accounting data, identifying potential failures before they impact our customers. • Defining metrics and benchmarks to provide the team with clear, quantitative insights into model and system performance. • Creating easy-to-use tooling that enables engineers to write, execute, and interpret evaluation tasks as a seamless part of their development workflow. • Collaborating closely with our Applied AI and Agent Engineering teams to guarantee every shipped capability has a well-defined standard of "good enough"—and a robust method to verify it. What We're Looking For • Experience writing and reviewing evaluation tasks used by AI researchers to assess and improve model performance. • Background in quality assurance across software, client deliverables, or financial analysis. • Exceptional written communication skills, with the ability to clearly articulate steps to achieve desired outcomes. • (Preferred) Familiarity with accounting, financial systems, tax preparation, or payment technologies.