Python Senior Software Engineer, AI Training

G2i Inc.
Worldwide Remote
RemoteCareer-pivot friendly

Who this role is best for

Best suited to senior-level engineers with experience in AI-assisted development working in the AI training domain.

Best fit for

  • Senior-level engineers with AI-assisted development experience and strong written communication skills
    — “Senior, Staff or Principal-level engineer (or equivalent experience)”
  • Candidates who can evaluate engineering judgment and reasoning, not just syntax
    — “Able to evaluate code without executing it or reviewing every line”
  • Individuals who can provide direct, opinionated feedback on AI interactions
    — “Comfortable giving direct, opinionated feedback”

Things to consider

  • The role may require adapting to a non-traditional evaluation workflow
    — “This is not a traditional engineering role”
  • The role necessitates a high level of written and spoken English proficiency
    — “Strong written and spoken English (B2 or above)”

How to stand out

  • Highlight experience in evaluating AI tools and providing constructive feedback
    — “Give clear, opinionated feedback in writing on what worked, what didn't”
  • Emphasize your ability to judge engineering reasoning beyond syntax
    — “Assess the quality of explanations and reasoning, not just the code”
  • Showcase your deep familiarity with AI-assisted development practices
    — “Deep familiarity with modern AI-assisted dev workflows”
  • Demonstrate your capability to define and articulate what great engineering looks like
    — “Help define what great looks like when working with tools like Cursor”
Pace · SteadyCollaboration · LowAutonomy · HighDecision Impact · Individual

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • AI-generated coding interactions end-to-end evaluation
  • useful and correct outputs
  • quality explanations and reasoning
  • clear feedback
Typical background
Senior, Staff or Principal-level engineerstrong background in TypeScript/JavaScript or Pythonhands-on experience with AI coding agents

Skills & requirements

Required

AI Coding Agents EvaluationEngineering JudgmentCode Quality AssessmentAi-assisted Dev WorkflowsTechnical Feedback

Preferred

Prompt DesignEvaluation WorkflowsMentoringEngineering Standards

Stack & domain

PythonTypescript/javascriptOpenai CodexClaude CodeCursorAi-assisted Dev WorkflowsPrompt DesignEvaluation WorkflowsJudgmentCommunicationFeedbackOpinionatedRigorousClearAICodingEngineering

About the role

Original posting from G2i Inc. via Ashby

Contract | Remote, worldwide | $100-$200/hour depending on experience and location | 10-20 hrs/week

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. Syntax correctness is the easy part.

WHAT YOU'LL BE DOING

  • Evaluate AI-generated coding interactions end to end
  • Judge whether outputs are useful, correct at a high level, and aligned with how a strong engineer would think
  • Assess the quality of explanations and reasoning, not just the code
  • Distinguish between levels of response quality (what makes something a 2 vs a 4)
  • Give clear, opinionated feedback in writing on what worked, what didn't, and what felt off or misleading
  • Help define what great looks like when working with tools like Cursor, Codex and Claude Code

WHAT WE MEAN BY "TASTE"

We're 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, and explaining them clearly.

WHO YOU ARE

  • 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 dev workflows
  • Able to evaluate code without executing it or reviewing every line
  • Strong written and spoken English (B2 or above). You'll be writing detailed feedback and recording short video explanations, so this is a hard requirement
  • Comfortable giving direct, opinionated feedback
  • High bar for what good engineering looks like

NICE TO HAVE

  • Prior exposure to prompt design or evaluation workflows
  • Experience mentoring senior engineers or defining engineering standards

ENGAGEMENT DETAILS

  • Rate: $100-$200/hour depending on experience and location
  • Hours: 10-20 hours/week, flexible
  • Duration: ongoing. Projects run from about two weeks to a few months each, and we offer new ones to evaluators who do well
  • Start: as soon as you clear the take-home and a project has an open seat
  • Process: one take-home evaluation exercise with a recorded Loom walkthrough. No interview

Source: G2i Inc. careers (Ashby)

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