AI Evaluator | Staff Software Engineer

Staff Software Engineer (AI Evals)

Contract | 20-40 hrs/week

We’re looking for highly experienced software engineer 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:

  • Go

  • Python

  • Rust

  • TypeScript / JavaScript

• 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

• Hours: ~20 hours+

• Duration: Short-term, starting from 2 weeks to 6 months

• Start: As soon as a project starts

• Process:

  • Take-home evaluation exercise

  • Background Check

  • Offer