[All remote jobs](https://jobicy.com/jobs.md)[![OpenAI logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2023/03/0523b13262b12c215d8009938f5c14f1.jpeg)](https://jobicy.com/company/openai.md)[OpenAI](https://jobicy.com/company/openai.md) # Support Delivery Lead – Toronto AI Summary OpenAI is seeking a senior Support Delivery Lead to build and lead a high-performing technical support engineering organization for strategic enterprise customers. The role owns complex escalations, operational scaling, and global 24x7 support coverage while serving as a key bridge among customers, Engineering, Product, Sales, and Technical Success. This leader will establish scalable processes, improve tooling and automation, and translate support insights into product and engineering roadmap improvements. The position requires substantial technical depth in application development or infrastructure alongside mature people leadership and customer-facing incident management. Although currently remote in Ontario, the role is expected to move to an in-office arrangement in Toronto.[Apply for this job](#job-application)[View company](https://jobicy.com/company/openai.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 297k–330k / yrDepartment[Technical Support](https://jobicy.com/categories/technical-support.md)EmploymentFull TimeExperienceSeniorPublished3 Nov 2026Apply before3 Dec 2026Listing views47Application actions3Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. About the Team OpenAI’s User Operations team shepherds our customer’s 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 24×7 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 24×7 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: * Have 5+ years of experience leading and managing technical support engineering or software engineering teams, ideally in high-scale or fast-paced environments. * Have 10+ years of experience in technical support engineering or software engineering * Have experience leading highly skilled engineering teams and are comfortable empowering senior ICs while setting a clear technical and operational direction. * Bring deep technical experience in application development or infrastructure, paired with a strong instinct for operational systems and customer reliability. * Are a strong cross-functional partner with a proven ability to influence engineering and product roadmaps through support-driven insights. * Take an automation-first approach and have a track record of implementing tooling or processes that scale support impact through AI and systems thinking. * Thrive in ambiguous environments and balance strategic leadership with a willingness to get into technical details when needed. * Are energized by customer impact and excel at building trust with strategic accounts during critical issues or periods of transformation. * Are mission-driven, collaborative, and operate 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. For additional information, please see [OpenAI’s Affirmative Action and Equal Employment Opportunity Policy Statement](https://cdn.openai.com/policies/eeo-policy-statement.pdf). 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](https://form.asana.com/?d=57018692298241&k=5MqR40fZd7jlxVUh5J-UeA). 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](https://form.asana.com/?k=bQ7w9h3iexRlicUdWRiwvg&d=57018692298241). [OpenAI Global Applicant Privacy Policy](https://cdn.openai.com/policies/global-employee-and-contractor-privacy-policy.pdf) 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. Show more [Apply now >](https://jobicy.com/jobs/158765-support-delivery-lead-toronto.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a highly senior leadership role requiring 10+ years of technical support or software engineering experience and at least five years managing technical teams. It combines critical enterprise escalations, organizational design, 24x7 operational responsibility, and cross-functional influence in an ambiguous, high-scale AI environment. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Highly competitiveC$313,500CA market range (per year)C$250k–C$360k0C$396.00k AI insightThe employer discloses a yearly base compensation range of CAD 297,000–330,000, with a midpoint of CAD 313,500. This is a credible range for a senior Toronto-based technical support and operations leader at a high-growth AI company. Estimated Canadian market compensation for a comparable senior support engineering leadership role is CAD 250,000–360,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [Technical support leadership](https://jobicy.com/jobs?search_keywords=Technical%20support%20leadership.md)[Support engineering](https://jobicy.com/jobs?search_keywords=Support%20engineering.md)[Incident management](https://jobicy.com/jobs?search_keywords=Incident%20management.md)[Enterprise customer support](https://jobicy.com/jobs?search_keywords=Enterprise%20customer%20support.md)[People management](https://jobicy.com/jobs?search_keywords=People%20management.md)[Application development](https://jobicy.com/jobs?search_keywords=Application%20development.md)[Infrastructure troubleshooting](https://jobicy.com/jobs?search_keywords=Infrastructure%20troubleshooting.md)[Operational excellence](https://jobicy.com/jobs?search_keywords=Operational%20excellence.md)[Process improvement](https://jobicy.com/jobs?search_keywords=Process%20improvement.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Technical escalation management](https://jobicy.com/jobs?search_keywords=Technical%20escalation%20management.md)[Automation strategy](https://jobicy.com/jobs?search_keywords=Automation%20strategy.md)[Customer reliability](https://jobicy.com/jobs?search_keywords=Customer%20reliability.md)[24x7 operations](https://jobicy.com/jobs?search_keywords=24x7%20operations.md) Sample interview questionsHow would you design a support engineering organization to provide reliable 24x7 coverage for strategic enterprise customers?I would begin by defining severity levels, escalation paths, ownership boundaries, and measurable service objectives. I would build geographically distributed coverage with clear handoffs, incident-command practices, and an on-call model that protects sustainable team capacity. I would also invest early in runbooks, observability, automation, and recurring reviews so that repeat issues are eliminated rather than repeatedly escalated. Tell us about a time you used support insights to influence an engineering or product roadmap. In a previous role, I consolidated escalation data, customer impact, reproduction patterns, and support effort into a prioritized problem statement for Engineering. By connecting recurring technical issues to reliability risk and enterprise retention, I secured roadmap investment in product instrumentation and self-service remediation. The resulting changes reduced repeat escalations and gave customers clearer diagnostics. How do you lead a team through a critical customer incident involving senior stakeholders? I establish a single accountable incident lead, a clear communication cadence, and separate technical and stakeholder communication channels. I ensure the team focuses on stabilization, evidence gathering, and safe mitigation while providing customers with transparent updates that distinguish confirmed facts from ongoing investigation. After resolution, I lead a blameless review with concrete preventive actions, owners, and deadlines. What does an automation-first support strategy mean in practice? It means identifying high-volume or high-effort diagnostic and remediation work, then improving it through product telemetry, internal tools, guided workflows, and customer-facing documentation. I prioritize automation where it reduces time to resolution, improves consistency, and frees expert engineers for novel issues. I measure impact through deflection, resolution time, recurrence, customer satisfaction, and engineering escalation rates. How do you balance empowering senior individual contributors with maintaining a consistent operating direction? I set explicit outcomes, decision rights, operating principles, and quality expectations, then give senior ICs ownership over the technical approach. Regular reviews ensure their work remains connected to customer impact, reliability goals, and organizational priorities without creating unnecessary approval layers. This balance builds trust, develops leaders, and preserves accountability for the overall service model. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. * ![OpenAI logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2023/03/0523b13262b12c215d8009938f5c14f1.jpeg) OpenAI Nov 3 New ### [Senior Support Engineer – Toronto](https://jobicy.com/jobs/158773-senior-support-engineer-toronto.md) About the Team The Technical Support team is responsible for ensuring that developers and enterprises can reliably build mission critical solutions using OpenAI models. We provide technical guidance, resolve complex… * ![Dropbox logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/09/WRILS-200923071227-398427.jpg) Dropbox Nov 3 New ### [Product Support Representative](https://jobicy.com/jobs/158624-product-support-representative-2.md) Role Description In this role, you will provide exceptional support for Dropbox Sign and DocSend! We use tools such as Slack, Jira, Zendesk, and Zoom to communicate with our users,… * ![NCR Voyix logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/2fcbc094-221.png) NCR Voyix Nov 3 New ### [Customer Engineer – Auckland](https://jobicy.com/jobs/148936-customer-engineer-auckland.md) About NCR VOYIXNCR Voyix Corporation (NYSE: VYX) is a global platform-powered leader in unified commerce for shopping and dining. Combining a flexible, intelligent platform with end-to-end payments capabilities and services… * ![Luxury Presence logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/05/f2b241fb769140fff2f70e8efaf5c0ff.jpg) Luxury Presence Nov 2 New ### [Online Support Representative](https://jobicy.com/jobs/158534-online-support-representative.md) Luxury Presence is building the AI growth platform for real estate. Backed by Bessemer Venture Partners and other top investors, we’re a Series C company that has hit $100M in… * ![Playson logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/6f266d9c-221-1.png) Playson Nov 2 New ### [Technical Support Engineer – night shifts](https://jobicy.com/jobs/158523-technical-support-engineer-night-shifts.md) Playson is a leading online gaming supplier, founded in 2012, which has developed worldwide recognition in the industry. We offer complete gaming solutions based on the latest technologies and detailed… * ![QuickNode logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/e4603221-221.png) QuickNode Nov 2 New ### [Technical Support Engineer](https://jobicy.com/jobs/154390-technical-support-engineer.md) Quicknode is a cloud-based infrastructure company that powers the blockchain ecosystem. Our mission is to be the indispensable utility that empowers companies and innovators globally to build next-generation, Web3 enabled… * ![BigID logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/09d6c6d2-221.jpg) BigID Nov 2 New ### [Professional Services Engineer](https://jobicy.com/jobs/152173-professional-services-engineer.md) Who we are: BigID is an innovative tech startup that focuses on solutions for data security, compliance, privacy, and AI data management. We’re leading the market in all things data:… * ![Roboflow logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/06/8cd75e4b-221.webp) Roboflow Nov 2 New ### [Implementation Engineer](https://jobicy.com/jobs/152223-implementation-engineer-3.md) Who We Are Our mission is to make the world programmable. Sight is one of the key ways we understand the world, and soon this will be true for the… * ![GitLab logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/12/WRILS-201207055737-109952.jpg) GitLab Nov 1 ### [Senior Support Engineer](https://jobicy.com/jobs/158332-senior-support-engineer-3.md) GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50… * ![Halter logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/fe337305-221.png) Halter Nov 1 ### [Field Specialist (Taranaki)](https://jobicy.com/jobs/158311-field-specialist-taranaki.md) About Halter At Halter, we’re on a mission to enable farmers and graziers to run the most productive and sustainable operations. Our customers are using Halter to break free from… [Browse all jobs](https://jobicy.com/jobs.md)