Job Description
Senior AI Interaction Evaluator (Codex / Claude Code)
Contract | $100-$200/hour | 10-20 hrs/week | Start ASAP (through early May)
Check out this Loom video for more details!
We're looking for 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 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
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 / 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
Contract | $100-$200/hour | 10-20 hrs/week | Start ASAP (through early May)
Check out this Loom video for more details!
We're looking for 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 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
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 / 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
💡 Quick Summary
Seeking a career-building opportunity? The Senior Engineer - AI Evaluator position is now open for candidates interested in the IT Engineer & Developer Jobs sector. This role in Chicago offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in IT Engineer & Developer Jobs is a plus.
