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Software Engineer; Trajectory

Job in Winnipeg, Manitoba, A3C, Canada
Listing for: Weekday AI (YC W21)
Full Time, Part Time position
Listed on 2026-06-16
Job specializations:
  • Software Development
Salary/Wage Range or Industry Benchmark: 70 - 130 CAD Hourly CAD 70.00 130.00 HOUR
Job Description & How to Apply Below
Position: Software Engineer (Trajectory)
This role is for one of our clients
Compensation: $70-$130 per hour

Location Requirements
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We are seeking experienced Software Engineers to contribute to high-impact research collaborations with leading AI labs. In this role, you will help build high-quality training datasets that enhance AI models' reasoning and problem-solving capabilities on real-world software engineering tasks. This is a unique opportunity to apply your practical development experience to advance the next generation of intelligent systems.

Requirements
You will work on annotating frontier-model trajectories across SWE-bench-style tasks derived from real-world open-source repositories. Since many closed-source models do not expose internal reasoning traces, this project focuses on reconstructing and annotating the reasoning process behind model-generated solutions.

Using your own problem-solving expertise and the full technical context of each task, you will infer and articulate the underlying chain-of-thought that explains how a solution is derived step by step.

Key Responsibilities

Review model-generated code trajectories on realistic software engineering tasks

Reconstruct detailed reasoning steps that explain the solution process

Annotate key decision points, debugging logic, and problem-solving strategies

Analyze full task context, including codebases, issue descriptions, and test cases

Ensure annotations reflect accurate, realistic developer reasoning and technical soundness

Deliver structured, high-quality written explanations aligned with engineering best practices

Ideal Qualifications

2+ years of hands‑on software engineering experience working with real-world codebases

Bachelor's degree in Computer Science, Software Engineering, or a related field (advanced degree preferred)

Strong proficiency in Python, JavaScript, Type Script, or similar commonly used open‑source languages

Familiarity with Git workflows, pull requests, and issue tracking systems

Strong debugging and analytical skills

Ability to clearly articulate technical reasoning in structured written form

Project Details

Start Date:

Immediate

Duration: 1‑2 months

Commitment:
Part‑time (15‑25 hours per week, with flexibility up to 40 hours per week)

Fully remote with flexible scheduling

Application & Onboarding Process

Submit your resume

Participate in a short (approximately 15‑minute) AI‑based conversational interview to discuss your background and interest

Receive follow‑up communication within a few days regarding next steps and onboarding

Contract & Payment Terms

Engagement will be structured as an independent contractor agreement

Work can be completed remotely on your own schedule

Projects may be extended, shortened, or concluded early based on performance and business needs

Work assignments will not involve access to confidential or proprietary information from any employer, client, or institution

Payments are processed weekly via Stripe or Wise based on services rendered

Visa sponsorship is not available; H1‑B and STEM OPT candidates cannot be supported at this time

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