Senior Software Engineer - AI Interaction Evaluator

Role Description

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.

You will assess how AI coding agents behave in real-world scenarios — focusing on:

• Whether the response makes sense
• Whether the preamble and reasoning are useful
• Whether the output reflects strong engineering judgment
• Whether the interaction feels right to an experienced developer

This role is about engineering taste — not syntax correctness.

What You’ll Be Doing:

• Evaluate AI-generated coding interactions end-to-end
• Judge whether outputs are:
  • Useful
  • Correct (at a high level)
  • Aligned with how a strong engineer would think
• Assess the quality of explanations and reasoning, not just code
• Distinguish between different levels of response quality (e.g. what makes something a 2 vs 4)
• Provide clear, opinionated feedback on:
  • What worked
  • What didn’t
  • What felt “off” or misleading
• Help define what great looks like when interacting with tools like Cursor

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.

Qualifications

• Staff / Principal-level engineer (or equivalent experience)
• Strong background in one of the below:
  • TypeScript / JavaScript
  • Python
• Hands-on experience using:
  • OpenAI Codex
  • Claude Code
  • Cursor
• Deep familiarity with modern AI-assisted dev workflows
• Able to evaluate code without needing to fully execute or deeply review every line
• Comfortable giving direct, opinionated feedback
• High bar for what “good engineering” looks like

Nice to Have

• Experience with tools like Cursor or similar AI-first IDEs
• Prior exposure to prompt design or evaluation workflows
• Experience mentoring senior engineers or defining engineering standards

Engagement Details

• Rate: $100–$200/hour
• Hours: ~10–20 hours/week
• Duration: Through early May (with possible extension)
• Start: ASAP
• Process:
  • Take-home evaluation exercise
  • One behavioral interview