How to apply for AI Support Engineer - Toronto

About OpenAI

OpenAI is a frontier AI research and product company with teams working on alignment, policy, and security. The company posts specific opportunities it considers high impact, and it does not necessarily recommend working at other positions there. Candidates should read the 80,000 Hours career review about concerns of doing harm by working at a frontier AI company before applying.

About the role

This AI Support Engineer role sits in OpenAI's User Operations team, which is building what it calls the first post-AGI support team. You will work directly with customers through support tickets and live calls, troubleshooting high-impact and novel technical problems for customers ranging from early-stage startups to global enterprises. The work supports mission-critical systems built on OpenAI's platform and helps define world-class support in an AGI-driven future.

A typical day

A typical day likely involves working through support tickets and live calls with customers, troubleshooting high-impact technical issues, and coordinating with Sales, Technical Success, Product, or Engineering. Because the role is remote and the environment is fast-moving, you may also spend time documenting novel problems and helping shape how the team defines support. Exact daily routines are not described in the job details, so ask about team structure and on-call expectations in interviews.

Who OpenAI is looking for

• Experienced in technical support or a customer-facing engineering role, comfortable handling support tickets and live calls with enterprise and startup customers.
• Deeply curious and able to resolve novel, ambiguous technical problems in a fast-moving environment.
• Skilled at working across teams, since the role partners closely with Sales, Technical Success, Product, and Engineering.
• Interested in AI adoption and able to guide customers on maximizing value from OpenAI's products at scale.

Tips for this application

• Read the 80,000 Hours career review on working at an AI lab before applying, and be ready to discuss your reasoning in your application.
• Show concrete examples of resolving ambiguous technical problems in support tickets or live calls, not just general customer service experience.
• Mention specific experience supporting enterprise customers or startups deploying AI products, since the role serves both segments.
• Highlight any work you have done with cross-functional partners such as Sales, Product, or Engineering to resolve customer issues.
• Note that this is a remote role based in Toronto; confirm your ability to work in that location and time zone in your application.

What to cover in your cover letter

Explain why you want to work at a frontier AI company and how you have weighed the concerns raised in the 80,000 Hours career review. Describe a specific complex or ambiguous technical issue you resolved for a customer through a support ticket or live call. Show how you have worked with Sales, Product, or Engineering to improve customer outcomes. State your interest in helping define support for an AGI-driven future and what that means to you.

Research before applying

• Read the 80,000 Hours career review on working at a frontier AI company and note your own position on the concerns it raises.
• Study OpenAI's product documentation and customer-facing materials to understand what customers deploy and where they commonly need support.
• Look into OpenAI's User Operations team and any public information about how it supports customers at scale.
• Check OpenAI's alignment, policy, and security work to understand the company's stated priorities beyond product.

Likely interview topics

Based on the job description, expect questions about:

• How you would troubleshoot a novel, ambiguous technical issue reported by an enterprise customer on OpenAI's platform.
• Your approach to handling a high-impact support ticket or live call when the root cause is unclear.
• How you have worked with Sales, Technical Success, Product, or Engineering to resolve customer issues.
• Your views on what world-class support looks like in an AGI-driven future.
• How you think about the concerns of working at a frontier AI company, as described in the 80,000 Hours career review.

Common mistakes to avoid

• Applying without addressing the ethical concerns of working at a frontier AI company, since OpenAI explicitly points candidates to the 80,000 Hours career review.
• Giving generic customer support examples instead of specific technical troubleshooting in tickets or live calls.
• Ignoring the cross-functional nature of the role and failing to mention experience with Sales, Product, or Engineering partners.