AI Software Engineer - Winnipeg

Salary: $90,000 - 130,000 per year Requirements:

• We bring at least 2 years of experience in backend engineering, AI automation, or complex systems integration.
• We have demonstrated success building and supporting production-ready software with clear modular boundaries, such as separate services for parsing, logic handling, and reporting.
• We are proficient in at least two major programming languages, such as Python, JavaScript, Go, or Java, and we have experience working with SQL databases.
• We have hands-on experience developing for live, non-simulated environments and managing multi-step system interactions.
• We have exceptional attention to detail and can deliver precise, high-value technical feedback on sophisticated system behavior.
• We have experience creating multi-stage coordination workflows where information gathering leads to reasoned outcomes.
• We are comfortable connecting agents with live tools such as Supabase, Gmail, and other APIs to solve practical problems.
• We are familiar with maintaining persistent state and session tracking using MEMORY.md to monitor agent progress.
• We can spot subtle issues such as privacy leaks, authority escalation, and indirect prompt injection.

• We will help train advanced AI systems by providing human feedback that improves agent performance.
• We will support the development of large language models so they can act as proactive, multi-step agents.
• We will contribute to projects that teach systems how to design, coordinate, and refine complex real-world architectural workflows.
• We will evaluate intricate system behavior and provide clear, detailed technical observations.
• We will collaborate with leading AI organizations to advance generative systems toward more capable orchestration.
• We will work on tasks that involve data collection, reasoning, and multi-stage execution.
• We will identify and surface failures or risks in agent behavior to improve reliability and safety.

• AI
• Backend
• Support
• Java
• JavaScript
• Python
• SQL

More:

We are Outlier, and we help some of the worlds most innovative companies improve their AI agents through human feedback. Our work focuses on training large language models to operate as proactive, multi-step agents that can design, coordinate, and optimize complex real-world workflows. We collaborate with leading AI organizations on advanced generative systems and welcome both orchestration experts and experienced software developers who want to help shape the future of autonomous agents.

last updated 37 week of 2026