[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) # Senior Support Engineer – Toronto AI Summary OpenAI is seeking a Senior Support Engineer to resolve high-severity technical issues for strategic enterprise customers using its API platform. The role combines advanced production troubleshooting, incident leadership, observability, and support-process automation in partnership with Engineering and Infrastructure. The engineer will design monitoring and alerting workflows, improve incident readiness, conduct root-cause analysis, and maintain operational documentation. This is a low-volume, high-difficulty position requiring 8+ years in SRE, NOC, or technical operations environments. Although currently remote in Ontario, the role is expected to move to an in-office Toronto arrangement.[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 261k–290k / yrDepartment[Technical Support](https://jobicy.com/categories/technical-support.md)EmploymentFull TimeExperienceSeniorPublished3 Nov 2026Apply before3 Dec 2026Listing views37Application 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 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 issues and support customers in maximizing value and adoption from deploying our highly-capable models. We work closely with Technical Success, Product, Engineering and others to deliver the best possible experience to our customers at scale. We think from an automation-first mindset and leverage the latest in AI to scale our support operations. Join the Senior Support Engineering (SSE) team at OpenAI and help shape the future of Technical Support in the age of AI. About the Role We are looking for a Senior Support Engineer to collaborate directly with our strategic enterprise accounts and product teams, helping solve some of the most difficult problems faced by our Customers. You will be part of the best technical troubleshooting team 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. As a Senior Support Engineer, you will design and run operational processes to monitor our top strategic customers and a 24×7 response team. You’ll work closely with our Infrastructure and Engineering teams to deliver the best possible experience to customers at scale. 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 API platform. The nature of this role will be low volume, high difficulty. This Toronto-based role is currently remote and is expected to transition to an in-office arrangement. In this role, you will: * Be among the foremost technical and troubleshooting experts for our API platform at OpenAI. You are the last line of defense before the core Engineering team. * Proactively identify and implement opportunities to scale support operations by leveraging automation and advancements in AI technologies. Contribute to shaping the future of technical support in an AI-driven era. * Configure and use advanced monitoring and alerting workflows to proactively detect customer impacting issues in real time. * In partnership with engineering, contribute to reliability reviews and preparedness for new features, launches, or strategic customer requirement updates. Ensure that operational readiness (monitoring, alerting, and fallback plans) is in place for any such changes. * Design and refine incident response processes and documentation across strategic customers, engineering and support teams. * Analyze operational metrics and incident RCAs to identify areas for improvement. Proactively recommend and implement enhancements to monitoring dashboards, alert configurations, and support workflows. * Provide support coverage during holidays and weekends based on business needs. You might thrive in this role if you: * Have a Bachelor’s degree in Computer Science or a related field. A strong software engineering foundation is important for this role’s success. * Have 8+ years of experience in technical operations roles such as SRE/NOC, designing monitoring systems and resolving production issues in fast-paced and mission-critical environments. A strong track record of troubleshooting complex technical problems at the systems level. * Have deep familiarity with modern monitoring, alerting, and observability practices. Hands‑on experience setting up or managing metrics, logging, and tracing for distributed systems (e.g., understanding of SLIs/SLOs, alert tuning, dashboard creation). * Have proven experience leading incident response for high‑severity outages or service disruptions. Able to perform real‑time incident coordination, root cause analysis, and drive follow‑ups (post‑mortems, action items) to prevent recurrence. Knowledge of industry best practices for incident management and fault diagnosis. * Have strong skills in scripting or software engineering (e.g., Python or similar) to automate repetitive tasks and integrate tools. * Have solid understanding of cloud infrastructure and distributed systems fundamentals. Comfortable working with cloud services, load balancers, databases, and containerized applications. * Are effective at working cross‑functionally in a high‑trust environment. Strong communication skills to explain technical issues and resolutions to both engineering and non‑technical stakeholders. You can coordinate efforts across teams and are comfortable providing updates in the midst of an ongoing incident. 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/158773-senior-support-engineer-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 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior escalation role handling complex, customer-impacting distributed-systems incidents and serving as the final support layer before core Engineering. Success requires deep operational judgment, real-time incident coordination, and the ability to improve reliability at scale. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Market rateC$275,500CA market range (per year)C$240k–C$330k0C$363.00k AI insightThe employer discloses a yearly base compensation range of CAD 261,000–290,000, with a midpoint of CAD 275,500. The estimated Canadian market range for a senior technical support and reliability-focused engineering role is CAD 240,000–330,000 per year; this is an AI estimate, not verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Technical troubleshooting](https://jobicy.com/jobs?search_keywords=Technical%20troubleshooting.md)[Incident response](https://jobicy.com/jobs?search_keywords=Incident%20response.md)[Root cause analysis](https://jobicy.com/jobs?search_keywords=Root%20cause%20analysis.md)[Observability](https://jobicy.com/jobs?search_keywords=Observability.md)[Monitoring and alerting](https://jobicy.com/jobs?search_keywords=Monitoring%20and%20alerting.md)[Distributed systems](https://jobicy.com/jobs?search_keywords=Distributed%20systems.md)[Cloud infrastructure](https://jobicy.com/jobs?search_keywords=Cloud%20infrastructure.md)[Python scripting](https://jobicy.com/jobs?search_keywords=Python%20scripting.md)[Support automation](https://jobicy.com/jobs?search_keywords=Support%20automation.md)[SRE practices](https://jobicy.com/jobs?search_keywords=SRE%20practices.md)[SLI/SLO management](https://jobicy.com/jobs?search_keywords=SLISLO%20management.md)[Dashboard design](https://jobicy.com/jobs?search_keywords=Dashboard%20design.md)[Customer communication](https://jobicy.com/jobs?search_keywords=Customer%20communication.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md) Sample interview questionsDescribe a high-severity production incident you led from detection through resolution.I would explain the incident scope, customer impact, initial signals, and how I established an incident channel and clear ownership. I would outline the mitigation steps, stakeholder updates, root-cause investigation, and resulting preventive actions such as alert improvements, runbook updates, or architectural changes. How do you design effective monitoring and alerting for a distributed API platform? I begin with user-impacting service objectives and define SLIs around availability, latency, error rates, throughput, and dependency health. I use actionable alerts with tuned thresholds, dashboards for diagnosis, tracing and structured logs for correlation, and regularly review alert quality to reduce noise and missed incidents. How would you support a strategic customer reporting intermittent API failures that cannot be reproduced easily? I would first collect precise timestamps, request identifiers, affected endpoints, error patterns, and deployment or traffic context. I would correlate those data points with platform metrics, logs, traces, and dependency signals, communicate findings transparently, and create a focused investigation plan with Engineering if the issue indicates a platform defect. Give an example of a repetitive support workflow you would automate. I would automate incident triage enrichment by collecting relevant metrics, recent deploys, error-rate changes, customer context, and trace links when an alert fires. This reduces manual context gathering, speeds escalation decisions, and creates more consistent incident records. How do you communicate during an active incident to both engineering teams and non-technical stakeholders? I provide concise, regular updates covering confirmed impact, current mitigation, known facts, unknowns, and the next update time. I avoid speculation, tailor technical depth to the audience, and maintain a single source of truth so teams can coordinate without conflicting information. Next step ## Apply now. 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