Senior Software Engineer - Python

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! https://www.loom.com/share/b0d1b0bf24c44ae8b95dca84b9db60e5
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