Technical lead building safe, evaluable LLM agents and AI infrastructure for OpenLoop’s telehealth platform. Setting architecture, observability, retrieval, and model operations direction.
About the role
- Senior engineer evaluating AI coding agents such as Codex, Claude Code, and Cursor. Providing rigorous written and video feedback on engineering judgment, reasoning, and interaction quality.
Responsibilities
- Evaluate the quality of interactions with modern coding agents such as OpenAI Codex and Claude Code
- Evaluate AI-generated coding interactions end to end
- Judge whether outputs are useful, correct at a high level, and aligned with strong engineering judgment
- Assess the quality of explanations and reasoning, not just the code
- Distinguish between levels of response quality
- Give clear, opinionated written feedback on what worked, what did not, and what felt off or misleading
- Help define what great looks like when working with Cursor, Codex and Claude Code
- Record short video explanations of evaluations
Requirements
- Senior, Staff or Principal-level engineer (or equivalent experience)
- Strong background in TypeScript/JavaScript or Python
- Hands-on experience with at least one of OpenAI Codex, Claude Code or Cursor
- Deep familiarity with modern AI-assisted development workflows
- Able to evaluate code without executing it or reviewing every line
- Strong written and spoken English (B2 or above); required for detailed written feedback and short video explanations
- Comfortable giving direct, opinionated feedback
- High bar for what good engineering looks like
- Prior exposure to prompt design or evaluation workflows (nice to have)
- Experience mentoring senior engineers or defining engineering standards (nice to have)
- Must complete one take-home evaluation exercise with a recorded Loom walkthrough
- Must agree to a simple background check for this project
Benefits
- Flexible hours: 10–20 hours/week
- Ongoing project opportunities for evaluators who do well
- Projects lasting about two weeks to a few months
- Start as soon as the take-home is cleared and a project has an open seat
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