Senior Support Engineer - Toronto

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 24x7 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 role is based remotely in Toronto, Canada. 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.