Dedicated Support Engineer - Toronto

OpenAI’s User Operations team ensures that customers' product experience is exceptional. We resolve complex issues, provide technical guidance, and support customers in maximizing value and adoption from deploying our products.

The Support Engineering team works closely with Engineering, Product, Technical Success, Go-to-Market, and other teams to deliver an exceptional experience for our most strategic customers. We combine deep technical troubleshooting with durable customer context, proactive reliability work, and clear ownership during critical moments.

We’re looking for experienced, deeply curious technical problem-solvers to serve as trusted support partners for our Premium Support customers. You’ll work directly with customers on novel, ambiguous, and high-impact technical issues, using logs, telemetry, reproduction, and systems-level investigation to isolate causes and drive issues toward resolution.

Responsibilities

• Work directly with Premium Support customers to troubleshoot their most complex technical issues, including API failures, integration challenges, authentication errors, unexpected product behavior, performance degradation, and production incidents.
• Provide end-to-end technical ownership by analyzing logs and system behavior, reproducing errors, testing hypotheses, and isolating the likely failure domain.
• Become a trusted expert on OpenAI’s products and systems, serving as a critical escalation point and a technical backstop for our most strategic customers.
• Own the customer-specific response to high-impact incidents.
• Communicate clearly and proactively during periods of uncertainty, providing accurate updates to customer technical teams, business stakeholders, executives, and internal partners.
• Develop a detailed understanding of each customer’s architecture, integrations, dependencies, critical workloads, and operational constraints.
• Partner with Go-to-Market and Technical Success teams to understand the business importance of customer workloads and ensure that relevant commercial context informs severity, prioritization, and communication.
• Represent Support Engineering in relevant customer meetings, including QBRs, and partner closely with account teams to communicate technical health, surface risks and blockers early, coordinate follow-up, and provide customers and internal stakeholders with clear, proactive updates.
• Monitor customer integrations and support trends to identify emerging risks, recurring failure patterns, and readiness gaps before they become major escalations.
• Prepare for important launches, migrations, traffic increases, and business events by developing account-specific runbooks, validating escalation paths, coordinating support readiness, and providing heightened monitoring where needed.
• Lead or contribute to incident reviews and postmortems, identify opportunities to prevent recurrence, and track corrective actions through closure.
• Translate recurring customer pain into clear, evidence-backed feedback for Product and Engineering.
• Turn what you learn from customer investigations into scalable improvements, including troubleshooting guides, monitoring, internal tooling, support workflows, and AI-powered automation.
• Help shape the operating model, technical standards, and tooling for Premium Support as the function grows globally.

Requirements

• Significant experience in Support Engineering, Solutions Engineering, Solutions Architecture, or another role involving hands-on diagnosis of complex production issues.
• Expert-level troubleshooting skills and a strong track record of resolving ambiguous technical problems across APIs, distributed systems, cloud infrastructure, and enterprise integrations.
• Comfortable working with logs, metrics, traces, API requests, authentication flows, and customer-provided code or configurations.
• Experience leading or playing a central role in customer-impacting incidents.
• Can write code or scripts to reproduce issues, interrogate systems, automate repetitive work, and improve internal tools.
• Can communicate complex technical issues clearly to engineers, customer technical teams, business stakeholders, and senior leaders.
• Build strong, high-trust relationships with customers and cross-functional partners.
• Look beyond the immediate issue to identify patterns, improve the system, and prevent the same problem from recurring.
• Thrive in ambiguity, update quickly as new information emerges, and are willing to learn whatever is needed to get the job done.
• Bring a humble, team-first mindset, strong judgment, and a genuine eagerness to help both customers and colleagues succeed.