Dedicated Support Engineer - Toronto

About the Team

OpenAI’s User Operations team shepherds our customers’ 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

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 use automation, agents, and our own technology to help build the future of technical support.

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.

Beyond resolving individual issues, you’ll use your deep understanding of OpenAI’s infrastructure and products, together with each customer’s architecture and operating context, to anticipate risk and make their workloads more resilient over time. You’ll proactively monitor integrations, identify emerging failure patterns and architectural breakpoints, and work with customers and internal teams to address them before they become incidents. Success means that as a customer’s workloads mature and scale, the day-to-day effort required to support them decreases through better monitoring, runbooks, automation, and preventative improvements.

This Toronto-based role is currently remote and is expected to transition to an in-office arrangement.

In this role, you will:

• 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. Where possible, you’ll identify the root cause before escalating to Engineering; where that is not possible, you’ll provide a clear hypothesis and the evidence needed to accelerate Engineering’s investigation.

• 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. You’ll assess severity and business impact, initiate the appropriate response path, coordinate cross-functional responders, maintain clear ownership, and ensure issues move through mitigation, resolution, and post-incident follow-through.

• 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. You’ll document this context and make it accessible to Support, Product, and Engineering teams.

• 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 without bypassing established support processes.

• 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, with a particular focus on improving the reliability and performance of existing products, integrations, and deployments.

• 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.

You might thrive in this role if you:

• Have significant experience in Support Engineering, Solutions Engineering, Solutions Architecture, or another role involving hands-on diagnosis of complex production issues.

• Have expert-level troubleshooting skills and a strong track record of resolving ambiguous technical problems across APIs, distributed systems, cloud infrastructure, and enterprise integrations.

• Are comfortable working with logs, metrics, traces, API requests, authentication flows, and customer-provided code or configurations to understand system behavior and test hypotheses.

• Have experience leading or playing a central role in customer-impacting incidents, including severity assessment, technical coordination, stakeholder communication, root-cause analysis, and post-incident follow-through.

• Can write code or scripts to reproduce issues, interrogate systems, automate repetitive work, and improve internal tools. Experience with Python, JavaScript, or similar languages is valuable.

• Can communicate complex technical issues clearly to engineers, customer technical teams, business stakeholders, and senior leaders—especially when information is incomplete or evolving.

• Build strong, high-trust relationships with customers and cross-functional partners while maintaining clear and scalable ownership boundaries.

• 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.

• Are excited to use OpenAI’s products, agents, and emerging AI capabilities to transform how technical support operates at scale.

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.

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