Senior AI Interaction Evaluator (Codex / Claude Code) Contract | $100–$200/hour | 10–20 hrs/week | Start ASAP (through early May)

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 robust 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

📌 Senior Engineer - AI Interaction Evaluator - US and Canada only (Winnipeg)
🏢 G2i
📍 Winnipeg