Python Senior Software Engineer, Ai Training

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Python Senior Software Engineer, AI Training based in Canada.
We are seeking an experienced Python Senior Software Engineer to contribute to the evaluation and improvement of advanced AI coding agents. Rather than developing production software, you will use your engineering expertise to assess how AI models approach technical challenges, communicate solutions, and demonstrate sound engineering judgment. You will evaluate AI-generated coding interactions, examining their technical quality, reasoning, explanations, and usefulness from the perspective of an experienced developer. Your insights will help establish benchmarks for high-quality AI-assisted software development and improve the way these tools support engineering teams. This opportunity is ideal for a senior engineer who combines strong Python expertise with critical thinking and excellent communication skills. The engagement is fully remote, flexible, and project-based.
AccountabilitiesIn this role, you will evaluate AI-generated coding interactions and provide expert feedback to help improve the quality, reliability, and usefulness of AI-powered development tools.
Evaluate AI-generated coding interactions from beginning to end, assessing their overall quality and effectiveness.
Determine whether AI outputs are useful, technically sound at a high level, and aligned with the reasoning and practices of an experienced software engineer.
Assess the quality of explanations, reasoning, and recommendations rather than focusing exclusively on code correctness.
Differentiate between varying levels of response quality and apply consistent evaluation standards.
Provide clear, detailed, and opinionated written feedback on what works, what does not, and what may feel inaccurate, misleading, or ineffective.
Assess whether AI models guide developers effectively, provide meaningful context, and build trust through their interactions.
Help define and refine quality benchmarks for AI coding agents, including tools such as OpenAI Codex, Claude Code, and Cursor.
Record short video explanations to communicate evaluation findings and provide additional context.
RequirementsThe ideal candidate is a highly experienced software engineer with strong Python expertise, a deep understanding of modern AI-assisted development workflows, and the ability to make rigorous technical assessments.
Senior, Staff, or Principal-level software engineering experience, or equivalent professional expertise.
Strong professional background in Python, with additional experience in TypeScript or JavaScript also relevant.
Hands-on experience with at least one of the following AI coding tools: OpenAI Codex, Claude Code, or Cursor.
Deep familiarity with modern AI-assisted software development workflows.
Ability to evaluate code and technical responses without necessarily executing the code or reviewing every line.
Strong written and spoken English proficiency (B2 level or above), as the role involves detailed written feedback and recorded video explanations.
Confidence in providing direct, constructive, and well-supported opinions.
Excellent critical thinking and communication skills, with a high standard for engineering quality.
Ability to distinguish between technical correctness and genuinely useful engineering guidance.
Nice to have:
Previous exposure to prompt design, AI evaluation, or model assessment workflows.
Experience mentoring senior engineers or defining engineering standards and best practices.
Benefits
Competitive hourly compensation ranging from $100 to $200, depending on experience and location.
Fully remote contract opportunity, with worldwide availability subject to regional eligibility.
Flexible workload of approximately 10-20 hours per week.
Flexible working hours.
Ongoing engagement, with individual projects typically lasting from two weeks to several months.
Opportunities to participate in additional projects based on evaluation performance.
Potential to start as soon as the take-home assessment is completed successfully and a project position becomes available.
Streamlined selection process consisting of one take-home evaluation exercise and a recorded video walkthrough, with no interview required.
Opportunity to contribute to the development and evaluation of advanced AI coding technologies.
How Jobgether works:We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.
We appreciate your interest and wish you the best!
Why Apply Through Jobgether?
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