Applied AI Engineer - Winnipeg

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

• We bring at least 2 years of experience in backend engineering, AI automation, or integrating complex systems.
• We have demonstrated success building and supporting production-ready software with clear modular boundaries, such as separate services for parsing, logic, 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 practical experience operating in live, non-mocked environments and handling multi-step system interactions.
• We have exceptional attention to detail and can deliver concise, high-signal technical feedback on intricate system behavior.
• We have experience designing multi-stage coordination tasks where data gathering leads to reasoned outcomes.
• We are comfortable integrating agents with live tools such as Supabase, Gmail, and other APIs to solve real-world challenges.
• We understand how to implement persistent state and session discovery using MEMORY.md to monitor agent progress.
• We can identify subtle issues such as privacy leakage, authority escalation, and indirect prompt injection.

• We help train advanced generative systems by providing human feedback on AI agents.
• We contribute to improving autonomous agents by teaching them how to manage multi-step, real-world workflows.
• We support the design, coordination, and optimization of complex architectural processes.
• We work with leading AI organizations to refine large language models so they operate as proactive agents.
• We analyze system behavior in live environments and provide detailed technical observations.
• We evaluate agent interactions and identify failures that may affect safety, reliability, or performance.

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

More:

We are Outlier, and we help the worlds most innovative companies improve their AI agents through human feedback. Our projects focus on training large language models to act as proactive, multi-step agents capable of handling complex architectural workflows in real-world settings. We are looking for passionate orchestration specialists and experienced software developers who want to help shape the future of autonomous systems like OpenClaw and contribute to the development of advanced generative AI.

last updated 37 week of 2026