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Added 9 mins ago
Senior AI Engineer (Permanent)
CoreFactor Inc.
ON · Downtown Toronto (Underground city), Ontario
Full-time
…existing LLMs (e.g., OpenAI, Claude, Gemini, etc.) through API integration, prompt engineering, fine-tuning, or Retrieval-Augmented Generation…
Added 39 mins ago
Senior Software Engineer- SATCOM
Photon-IV
Canada
Full-time
…and guiding the technical direction of software projects. The lead engineer collaborates with wireless engineers, AI/ML specialists, and product stakeholders to translate mission…
Added 39 mins ago
Senior AI Engineer (Permanent)
CoreFactor
Toronto, ON · Greater Toronto Area, Canada
Full-time
…existing LLMs (e.g., OpenAI, Claude, Gemini, etc.) through API integration, prompt engineering, fine-tuning, or Retrieval-Augmented Generation…
Added 55 mins ago
Junior Solutions Engineer
Pontosense
Toronto, ON
Full-time
Toronto or Waterloo, hybrid | Full-time | Reports to the Solutions Lead
Added 1 hour ago
Junior Solutions Engineer
Pontosense
Toronto, ON
Full-time
Toronto or Waterloo, hybrid | Full-time | Reports to the Solutions Lead
Added 2 hours ago
Business Analyst - Regulatory Affairs and Delivery Modernization
Real Estate Council of Ontario
Toronto, ON
Proven ability to lead complex, multi-stakeholder initiatives with firm timelines.
Added 2 hours ago
Hardware Engineering Manager
Daanaa
Vancouver, BC
Full-time
We are growing here at Daanaa and are looking for a Hardware Engineering Manager to lead our hardware engineering team and drive the development of next-generation power electronics from…
Added 2 hours ago
Power Electronics Controls Engineer
Daanaa
Vancouver, BC
Full-time
Lead control-topology co-design to optimize converter architectures, switching strategies, and overall system performance.
Added 2 hours ago
Simulation Operations Specialist, Academic Health Sciences
University of Saskatchewan
Saskatoon, SK
Troubleshoot hardware and software issues; support IT integration.
Added 2 hours ago
Product Lead
Pontosense
Toronto, ON
Full-time
Lead the product that home care organizations and partners use to keep older adults safe, at a fast-growing senior care technology company in 24 countries.
Added 3 hours ago
Salesforce Commerce Cloud (SFCC) Architect
T&A IT SOLUTIONS
NB · Chiasson Office, NB
Full-time
We are seeking an experienced Salesforce Commerce Cloud (SFCC) Architect to lead the architecture, design, and delivery of enterprise-scale digital commerce solutions. The ideal candidate…
Added 3 hours ago
Backend Engineer (Golang)
Mai Wealth
Engineer, BC
Full-time
Work closely with the tech lead, UI/UX team, and leadership to define, design, build, test, and deploy the scalable products in the investment space in Vietnam.
Added 4 hours ago
Product Manager - AI
Simpro Software
Montreal, QC
Full-time
Ethics & Governance: Lead product-level considerations for AI ethics and compliance, ensuring automated decision-making meets industry standards for our partners.
Added 4 hours ago
Geomodeller/Structural Geologist
GEI Consultants, Inc.
London, ON
$90,000 to $115,000 CAD / year
Full-time
…strengthening our local roots while expanding our reach. This integration brings together deep regional knowledge, a legacy of trusted relationships, and the technical excellence GEI is…
Added 5 hours ago
Financial Manager
Husky Technologies
Bolton, ON
Full-time
During the month end close, review process and integration issues in BAAN and AX. Liaison with IT and/or Controllership to resolve prior to the period close. This requires a comprehensive…
Added 5 hours ago
Industrial Software Validation|
Husky Technologies
Bolton, ON
Full-time
…passion of our people around the world and their desire to lead change. At the same time, we are not afraid to expect a lot and strive for leadership in all of our key markets. We are a…
Added 6 hours ago
Delivery Manager (Professional Services)
Resonaite
Toronto, ON
$115,000 to $120,000 CAD / year
Full-time
We are seeking a Delivery Manager to lead the successful delivery of client technology initiatives while providing day-to-day leadership to a highly skilled technical team.
Added 6 hours ago
Generative Artists
Terribly Wonderful
Toronto, ON
Full-time
Lead Generative Artist – Animated Feature Film
Added 7 hours ago
Senior Systems Engineer
Aviso
Toronto, ON
$110,000 to $120,000 CAD / year
Full-time
Lead or actively contribute to infrastructure projects, including platform upgrades, migrations, patching programs, automation initiatives, Azure deployments, DR improvements, monitoring…
Added 7 hours ago
Solution Architect
Aviso
Toronto, ON
$150,000 to $168,000 CAD / year
Full-time
…partner with business stakeholders and solutioning teams to lead and drive the implementation of technology solutions incrementally towards the enterprise architectural…
Added 8 hours ago
Product Owner - Asset Management, Temporary
Aviso
Toronto, ON
Full-time
…cross-functional teams; building trust and encouraging inclusion. You will lead your team towards peak performance, providing regular coaching, removing roadblocks, and providing the…
Added 8 hours ago
Product Owner - Asset Management, Temporary
Aviso Wealth
Remote, Canada
$70 to $85 CAD / hour
Full-time · Remote
…cross-functional teams; building trust and encouraging inclusion. You will lead your team towards peak performance, providing regular coaching, removing roadblocks, and providing the…
Added 8 hours ago
Product Owner - Asset Management, Temporary
Aviso Wealth
Remote, Canada
$70 to $85 CAD / hour
Full-time · Remote
…cross-functional teams; building trust and encouraging inclusion. You will lead your team towards peak performance, providing regular coaching, removing roadblocks, and providing the…
Added 9 hours ago
Lead Specialist – IT SAP Supply Chain (MM)
Parkland Corporation
Calgary, AB
Full-time
…Maintenance (PM) and Technical teams (Basis, Security, Development,…
Added 9 hours ago
Lead Specialist – IT SAP Supply Chain (MM)
Parkland Corporation
Calgary, AB
Full-time
…Maintenance (PM) and Technical teams (Basis, Security, Development,…

OpenAI

Dedicated Support Engineer - Toronto

Canada

Job type: Full-time
Posting language: English
Posted: Sep 25, 2026

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Original job description

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.

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.

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. 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.

OpenAI Global Applicant Privacy Policy

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.

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More about this job

Responsibilities

You will troubleshoot complex technical issues for strategic customers, including API failures and production incidents, while providing end-to-end technical ownership. Additionally, you will proactively monitor integrations and collaborate with internal teams to improve system reliability and performance.

Requirements

The role requires significant experience in Support or Solutions Engineering with expert-level troubleshooting skills across distributed systems and cloud infrastructure. Candidates must be proficient in languages like Python or JavaScript and possess strong communication skills to manage high-impact incidents.

Skills

Technical Troubleshooting
API
Distributed Systems
Cloud Infrastructure
Enterprise Integrations
Python
JavaScript
Incident Management
Root Cause Analysis
Telemetry
Automation
Customer Success
Systems Architecture
Data Analysis
Communication

Visa sponsorship

Not detected in the job text

Keywords

Support Engineering
Solutions Engineering
Solutions Architecture
API
Distributed Systems
Cloud Infrastructure
Enterprise Integrations
Python
JavaScript
Telemetry
Automation
Incident Management
Root Cause Analysis
Postmortem
QBR
Technical Support
Reliability
Monitoring
Authentication
Performance Degradation
Runbooks
Customer Success
Stakeholder Management
System Architecture
Data Analysis

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