Head of Support Engineering at OpenAI | Career Growth - Remote

This is a senior leadership role at one of the most high-profile AI companies in the world, making it a rare opportunity for experienced engineering managers ready to operate at the frontier of AI deployment. Building a team "from first principles" at OpenAI signals both significant autonomy and significant accountability.

Compensation context: No salary is listed, which is common for senior leadership roles at OpenAI. Based on market data, comparable Director/Head of Support Engineering roles at top-tier AI/tech companies in Canada typically range from CAD $180,000-$280,000+ base, with meaningful equity upside. OpenAI's compensation packages are known to be competitive globally.

- Scaling technical support operations in a hyper-growth, high-complexity AI workplace
- Cross-functional influence over product and engineering roadmaps
- Enterprise relationship management at the most strategic level
- AI-driven automation of support workflows - a highly transferable, in-demand skill set

Green flags: This is a true "builder" role - you're establishing a new function, which is excellent for career visibility. Direct access to Engineering and senior leadership is a strong signal of organizational trust and impact potential.

Red flags to consider: The 24x7 operational requirement and on-call expectations suggest a demanding work-life balance, especially in the early build phase. The transition from remote to in-office is also worth factoring into your personal situation before accepting.

Overall, this is a high-reward, high-demand role best suited to candidates who want to shape a legacy function at a defining company in AI history.

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 are looking for a leader to build and scale our Support Engineering team, which will collaborate directly with our strategic enterprise accounts, our product and engineering teams, as well as our field teams to solve some of the most difficult technical problems faced by our customers. You will lead one of the best technical troubleshooting teams at OpenAI, and our customers and Engineering teams will look to you for technical guidance in addressing the most technically difficult issues in our environment.

You will play an integral role in building knowledge within the team and be part of strategic initiatives for organizational and process improvements.



Working directly with our most strategic customers, you will be crucial to the success of the most innovative, disruptive, and high-scale AI solutions being built with the OpenAI platform.

This team will handle high difficulty situations and issues. The team will be global, providing 24x7 technical coverage for our customers. This will be an opportunity to build this new team from first principles - your leadership will determine the future of this organization.

The ideal candidate will have a combination of technical capabilities mixed with robust leadership and systems building strength.

This Toronto-based role is currently remote and is expected to transition to an in-office arrangement.

Key Responsibilities:

- Build and lead a team of the foremost technical and troubleshooting experts at OpenAI. You are the last line of defense before the core Engineering team.
- Partner with engineering and customer teams to build out our systems to ensure that we resolve escalated issues. You will engage with senior leaders internally or with customers and coordinate resources across multiple teams as needed.
- Take learnings from resolving customer issues and operationalize those solutions at scale, iterating on internal processes with Engineering/Go-To-Market/vendor partners, influencing product roadmaps, and improving overall customer experience with support.
- Manage scaling and operations of the team in order to deliver 24x7 coverage globally, including holidays and weekends based on business needs.
- Build strong relationships with our customers to ensure their application's success.
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📌 Head of Support Engineering at OpenAI | Career Growth (Toronto)
🏢 OpenAI
📍 Toronto