Senior Software Engineer - AI Interaction Evaluator

Senior AI Interaction Evaluator (Codex / Claude Code) Contract | $50-200/hr | 10–20 hrs/week | Start ASAP (through early May) Check out this Loom video for more details! We’re looking for a highly experienced software engineer (SR+) to help evaluate the quality of interactions with modern coding agents such as OpenAI Codex and Claude Code. This is not a traditional engineering role. You won’t be writing production code. You’ll be evaluating something harder: whether the model thinks like a great engineer. What This Role Actually Is You will assess how AI coding agents behave in real-world scenarios — focusing on: Whether the response makes senseWhether the preamble and reasoning are usefulWhether the output reflects strong engineering judgmentWhether the interaction feels right to an experienced developerThis role is about engineering taste — not syntax correctness. What You’ll Be Doing Evaluate AI-generated coding interactions end-to-endJudge whether outputs are:UsefulCorrect (at a high level)Aligned with how a strong engineer would thinkAssess the quality of explanations and reasoning, not just codeDistinguish between different levels of response quality (e.g. what makes something a 2 vs 4)Provide clear, opinionated feedback on:What workedWhat didn’tWhat felt “off” or misleadingHelp define what great looks like when interacting with tools like Cursor What We Mean by “Taste” We’re specifically looking for engineers who can answer questions like: Does this feel like something a strong engineer would actually say?Is this explanation helpful, or just technically correct?Is the model guiding the user well, or just dumping output?Would this interaction build or erode trust?You should be comfortable making subjective but rigorous judgments. Who You Are Staff / Principal-level engineer (or equivalent experience)Strong background in one of the below:TypeScript / JavaScriptPythonHands-on experience using:OpenAI CodexClaude CodeCursorDeep familiarity with modern AI-assisted dev workflowsAble to evaluate code without needing to fully execute or deeply review every lineComfortable giving direct, opinionated feedbackHigh bar for what “good engineering” looks like Nice to Have Experience with tools like Cursor or similar AI-first IDEsPrior exposure to prompt design or evaluation workflowsExperience mentoring senior engineers or defining engineering standards Engagement Details US and Canada up to $200/hrEU and Latam up to $150/hrOther locations up to $100/hr Hours: ~10–20 hours/weekDuration: Through early May (with possible extension)Start: ASAPProcess:Take-home evaluation exerciseOne behavioral interview