Senior Engineer - AI Interaction Evaluator - US and Canada only

Department: G2i Eng Team

Location: Miami, Calgary, Mississauga, Vancouver, Boston, Montreal, Denver, Oklahoma City, Nashville, Indianapolis, Chicago, Huston, Seattle, Chesapeake, Atlanta, Ottawa, Toronto, Austin, Norfolk, Dallas, Virginia Beach, San Antonio, Philadelphia, Arlington, Richmond, Savannah, Columbus, Las Vegas, Winnipeg, Boise, Fairfax, Fort Worth, Jacksonville, Edmonton, Reno, Washington, D.C.

Employment Type: Contract

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