AI Support Engineer - Toronto (Weekend Shift)
About this role
Deeply curious and dedicated professionals who enjoy navigating ambiguity and tackling complex technical challenges will find a natural fit in this User Operations team at OpenAI. The group shepherds customer adoption of AI platforms, resolving intricate issues and providing technical guidance to organizations ranging from early-stage startups to established global enterprises. Team members work directly with users through tickets and live calls to troubleshoot API failures, integration hurdles, and production incidents.
Operating within a fast-moving environment, the person in this role will also partner closely with Engineering, Product, and Operations to improve internal systems, reduce bugs, and scale support workflows. Responsibilities include leveraging automation and emerging AI capabilities to transform how support functions at scale while maintaining a standard work week that includes weekend coverage shifts. Success requires strong SaaS troubleshooting skills, enterprise communication abilities, and a collaborative mindset focused on customer value.
What you will do
- Work directly with customers to troubleshoot and resolve complex technical issues such as API failures, integration challenges, authentication errors, and production incidents.
- Provide end-to-end ownership through debugging logs, analyzing system behavior, reproducing issues, and delivering expert guidance.
- Serve as a critical escalation point and line of defense for complex technical problems while partnering with Engineering teams to proactively prevent recurring issues.
- Drive operational excellence by identifying opportunities for automation and AI-powered workflows to increase team efficiency.
- Take learnings from resolving customer issues to create scalable solutions in partnership with Product and Go-To-Market teams.
- Provide occasional holiday and weekend support on call coverage as needed to meet business and customer needs.
What you need
- Have eight or more years of experience in User Operations, Engineering, Support Engineering, or similar technical roles within fast-paced environments.
- Demonstrate comfort using emerging technologies to script or engineer code for automating repetitive tasks and integrating tools.
- Possess expert-level SaaS troubleshooting skills with the ability to rapidly understand new technologies and complex concepts.
- Bring polished enterprise communication skills and maintain calmness with high-stakes customers during live incident calls.
- Show proven experience building strong relationships with customers and cross-functional partners to drive issue resolution.
- Hold a Bachelor's degree in Computer Science, Computer Engineering, another relevant technical field, or equivalent practical experience.
Skills and tech stack
Questions candidates ask
What is the remote work policy and location for this job?
The position is remote based in Ontario, with candidates required to work in Toronto.
What are the working hours and shift expectations?
Each person in this role is expected to work a standard 5x8 work week, with one of the days covering weekend shifts each week such as Tuesday through Saturday or Sunday through Thursday.
What tools and technologies will I be working with?
You will use emerging technologies like Codex, ChatGPT, OpenAI API, and Python to script or engineer code for automating repetitive tasks.
What kind of experience is required for this role?
Applicants need 8+ years of experience in User Operations, Engineering, Support Engineering or similar technical roles, ideally within high-growth tech startups or other fast-paced environments.