Head of Support Engineering at OpenAI | Career Growth
- Remote 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. 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. 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 Direct access to Engineering and senior leadership is a strong signal of organizational trust and impact potential. 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. 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. 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. The team will be global, providing 24x7 technical coverage for our customers. The ideal candidate will have a combination of technical capabilities mixed with strong leadership and systems building strength. This Toronto-based role is currently remote and is expected to transition to an in-office arrangement. 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. Ensure the team is assisting broadly where needed beyond the core remit of the team. Be a part of the broader leadership team in Support. 5+ years of experience leading and managing technical support engineering or software engineering teams, ideally in high-scale or fast-paced environments. 10+ years of experience in technical support engineering or software engineering. Experience leading highly skilled engineering teams and comfort empowering senior ICs while setting a clear technical and operational direction. Deep technical experience in application development or infrastructure, paired with a strong instinct for operational systems and customer reliability. Strong cross-functional partnership with a proven ability to influence engineering and product roadmaps through support-driven insights. Automation-first approach with a track record of implementing tooling or processes that scale support impact through AI and systems thinking. Ability to thrive in ambiguous environments and

📌 Head of Support Engineering at OpenAI | Career Growth (Toronto)
🏢 OpenAI
📍 Toronto