How to apply for Support Delivery Lead - Toronto

About OpenAI

OpenAI is a frontier AI research and product company. Teams work on alignment, policy, and security. This role sits within User Operations, which is building what it calls the first post-AGI support team.

About the role

You would lead the Support Engineering team that works directly with strategic enterprise accounts, plus product, engineering, and field teams. The focus is resolving the most technically difficult customer issues and building knowledge, process, and organizational improvements. You are expected to be a technical guide for customers and Engineering.

A typical day

You would likely spend time on difficult technical issues from strategic enterprise accounts, guiding your team and working with Engineering and Product. You would also work on team knowledge, process improvements, and strategic initiatives for the support organization. The job post does not describe a fixed daily routine, so ask about team structure and on-call expectations in interviews.

Who OpenAI is looking for

• Has led a technical troubleshooting or support engineering team, ideally for enterprise or strategic accounts.
• Can personally engage with difficult technical issues in an AI product environment and guide engineers on them.
• Has worked cross-functionally with Sales, Technical Success, Product, and Engineering.
• Is comfortable building team knowledge, process improvements, and scaling a support function.

Tips for this application

• Show direct experience leading a support engineering or technical troubleshooting team, not just general customer support.
• Name specific enterprise or strategic accounts you have supported and the technical complexity involved.
• Describe how you built or scaled support processes, knowledge bases, or team structures.
• Reference OpenAI's User Operations framing as a post-AGI support team and explain how your background fits that.
• Avoid generic AI enthusiasm. Focus on technical troubleshooting leadership and enterprise customer outcomes.

What to cover in your cover letter

Emphasize your experience leading technical support or troubleshooting for enterprise customers. Give an example of resolving a difficult technical issue alongside product or engineering teams. Explain how you have built team knowledge or improved support processes. State why you want to work at a frontier AI company in a support leadership role.

Research before applying

• Read OpenAI's User Operations team description and what it says about being a post-AGI support team.
• Read the 80,000 Hours career review on working at an AI lab, which OpenAI links in the job post.
• Understand OpenAI's product surface relevant to enterprise customers, including API and deployment options.
• Look into OpenAI's alignment, policy, and security work to understand the company context.

Likely interview topics

Based on the job description, expect questions about:

• How you would build and scale a Support Engineering team for strategic enterprise accounts.
• A specific example of troubleshooting a complex technical issue and working with Engineering to resolve it.
• How you prioritize and manage difficult technical issues across multiple enterprise customers.
• How you build knowledge within a support team and drive process improvements.
• How you work with Sales, Technical Success, Product, and Engineering to deliver customer outcomes.

Common mistakes to avoid

• Applying without showing experience leading a technical support or troubleshooting team.
• Focusing on general customer service rather than technical troubleshooting for enterprise accounts.
• Ignoring the cross-functional nature of the role and not mentioning work with Sales, Product, or Engineering.