This is a high-prestige, high-impact senior technical role at one of the most prominent AI companies in the world. Working as the "last line of defense before the core Engineering team" signals genuine technical authority and visibility with executive-level enterprise customers.

Compensation:

No salary is disclosed, but Senior Support Engineer / SRE-equivalent roles at tier-1 AI companies in Toronto typically range from CAD $130,000–$190,000 annually, with equity potentiall y adding significant upside at OpenAI's valuation. The lack of disclosed pay is a minor yellow flag for transparency.

- Advanced observability engineering (SLIs/SLOs, distributed tracing) — extremely marketable in 2024–2025
- AI platform operations and enterprise API support — a niche with growing demand
- Incident command and cross-functional leadership at scale
- Automation and AI-augmented support tooling

Green flags:

"Automation-first mindset," direct collaboration with Engineering, and working on cutting-edge AI infrastructure are robust career accelerators. The role bridges SRE and customer-facing technical leadership — a rare hybrid.

Red flags:

Holiday and weekend coverage requirements suggest potential work-life balance strain. The in-office transition removes remote flexibility. At 8+ years experience required, this is a senior role but the title "Support Engineer" may underrepresent the seniority to external recruiters — worth clarifying during negotiation.

Overall, strong career move for SREs or technical ops leaders who want to be at the frontier of AI deployment.

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 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 — 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

📌 Senior Support Engineer at OpenAI (Toronto)
🏢 OpenAI
📍 Toronto