AI Support Engineer - Toronto (Weekend Shift)

About this role

About the Team

OpenAI’s User Operations team shepherds our customers’ adoption of AI and ensures that our customers' product experience is nothing short of exceptional. We are building the very first post-AGI support team. We resolve complex issues, provide technical guidance, and support customers in maximizing value and adoption from deploying our products. We work closely with Sales, Technical Success, Product, Engineering and others, to deliver the best possible experience to our customers at scale. OpenAI's customers represent a range of diverse backgrounds and maturity, from early-stage startups to established global enterprises.

About the Role

We’re looking for dedicated, experienced, and deeply curious individuals to help solve some of the most complex challenges faced by our customers while building the future of post-AGI support alongside us. In this role, you’ll work directly with customers through support tickets and live calls, troubleshooting high-impact issues and resolving novel, often ambiguous technical problems in one of the fastest-moving environments in technology. As AI adoption rapidly accelerates, the work you do will directly support mission-critical systems being built on OpenAI’s platform, serving as a critical line of defense for customers operating at massive scale.

Beyond resolving technical issues, you’ll help define what world-class support looks like in an AGI-driven future. You’ll partner closely with Engineering, Product, and Operations to improve systems, reduce bugs, and elevate the customer experience, while leveraging automation, agents, and our own AI technology to transform how support operates at scale.

Note: each person in this role will be expected to work a standard 5x8 work week, with 1 of the days covering weekend shifts each week (e.g., work weeks covering Tuesday - Saturday or Sunday - Thursday)

You’ll be responsible for:

• Working directly with customers to troubleshoot and resolve their most complex technical issues, including API failures, integration challenges, authentication errors, and production incidents. Providing end-to-end ownership through debugging logs, analyzing system behavior, reproducing issues, and delivering expert guidance.