Head of Support Engineering at OpenAI | Career Growth

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 environment


• 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 strong 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.


• 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. You will have the opportunity to build not just within this team, but across the organization.

Qualifications:

• 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 balance strategic leadership with a willingness to get into technical details when needed.


• Energized by customer impact and excel at building trust with strategic accounts during critical issues or periods of transformation.


• Mission-driven, collaborative, and operating with high integrity and humility.

About OpenAI

OpenAI is an AI research and deployment company dedicated to ensuring that general-purpose artificial intelligence benefits all of humanity. We push the boundaries of the capabilities of AI systems and seek to safely deploy them to the world through our products. AI is an extremely powerful tool that must be created with safety and human needs at its core, and to achieve our mission, we must encompass and value the many different perspectives, voices, and experiences that form the full spectrum of humanity.

We are an equal opportunity employer, and we do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or other applicable legally protected characteristic.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the San Francisco Fair Chance Ordinance, the Los Angeles County Fair Chance Ordinance for Employers, and the California Fair Chance Act, for US-based candidates. For unincorporated Los Angeles County workers: we reasonably believe that criminal history may have a direct, adverse and negative relationship with the following job duties, potentially resulting in the withdrawal of a conditional offer of employment: protect computer hardware entrusted to you from theft, loss or damage; return all computer hardware in your possession (including the data contained therein) upon termination of employment or end of assignment; and maintain the confidentiality of proprietary, confidential, and non-public information. In addition, job duties require access to secure and protected information technology systems and related data security obligations.

To notify OpenAI that you believe this job posting is non-compliant, please submit a report through this form . No response will be provided to inquiries unrelated to job posting compliance.

We are committed to providing reasonable accommodations to applicants with disabilities, and requests can be made via this link .

At OpenAI, we believe artificial intelligence has the potential to help people solve immense global challenges, and we want the upside of AI to be widely shared. Join us in shaping the future of technology.

Is this OpenAI Support Engineering Manager role permanently remote? No. The role is currently remote but is explicitly expected to transition to an in-office arrangement in Toronto. Candidates should be prepared to eventually work from the Toronto office. What level of experience is required for this role? OpenAI requires 10+ years of experience in technical support engineering or software engineering, with at least 5+ years specifically in a leadership or management capacity, ideally in high-scale or fast-paced environments. Will this role require on-call or weekend availability? Yes. The team is designed to provide 24x7 global technical coverage, including holidays and weekends based on business needs, so the manager must be prepared to oversee operations during those periods. What is the salary range for this position? No salary range is listed in the job posting. Compensation details would be discussed during the interview process, but senior engineering leadership roles at top AI companies in Canada are typically highly competitive. What teams will the Support Engineering Manager collaborate with at OpenAI? This role works closely with Sales, Technical Success, Product, Engineering, Go-To-Market teams, vendor partners, and directly with strategic enterprise customers to resolve escalated technical issues and influence product roadmaps.

Remote work & career advice that actually works.