OpenAI

AI Support Engineer - Toronto (Weekend Shift)

OpenAI • $110K — $130K *
US-AnywhereRemote in Ontario, CA
Technical Services
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years of experience in User Operations, Engineering, or Support Engineering roles, preferably in fast-paced tech environments.
  • Proficiency with emerging technologies such as Codex and OpenAI API, including coding in Python for automation.
  • Expert-level troubleshooting skills in SaaS environments, with an ability to learn complex concepts quickly.
  • Strong communication skills for high-stakes interactions with enterprise customers during live calls.
  • History of building strong relationships with customers and cross-functional teams for effective issue resolution.
  • Exceptional problem-solving skills, capable of clearly articulating complex issues to diverse audiences.
  • Ability to thrive in ambiguous environments and adapt quickly to change.

Responsibilities

  • Troubleshoot and resolve complex technical issues, including API failures and integration challenges.
  • Become a trusted expert on OpenAI's platform, providing guidance on technical issues.
  • Act as a critical escalation point for complex problems, collaborating with Engineering to find solutions.
  • Create scalable solutions based on learnings from customer issues, working with Product and Go-To-Market teams.
  • Drive operational excellence by implementing automation and AI to improve support workflows.
  • Offer holiday and weekend on-call support as necessary to address customer needs.

Benefits

  • Flexible work hours with a standard 5x8 schedule, including one weekend day each week.
  • Opportunity to work with cutting-edge AI technologies and platforms.
  • Engagement with a diverse range of complex technical challenges.
  • Collaboration with Engineering and Product teams to influence future support operations.
Full Job Description
About the Role

We're looking for dedicated, experienced, and deeply curious individuals to help solve some of the most complex challenges faced by our customers while building the future of post-AGI support alongside us. In this role, you'll work directly with customers through support tickets and live calls, troubleshooting high-impact issues and resolving novel, often ambiguous technical problems in one of the fastest-moving environments in technology. As AI adoption rapidly accelerates, the work you do will directly support mission-critical systems being built on OpenAI's platform, serving as a critical line of defense for customers operating at massive scale.

Beyond resolving technical issues, you'll help define what world-class support looks like in an AGI-driven future. You'll partner closely with Engineering, Product, and Operations to improve systems, reduce bugs, and elevate the customer experience, while leveraging automation, agents, and our own AI technology to transform how support operates at scale.

Note: each person in this role will be expected to work a standard 5x8 work week, with 1 of the days covering weekend shifts each week (e.g., work weeks covering Tuesday - Saturday or Sunday - Thursday)

You'll be responsible for:
  • Working directly with customers to troubleshoot and resolve their most complex technical issues, including API failures, integration challenges, authentication errors, and production incidents. Providing end-to-end ownership through debugging logs, analyzing system behavior, reproducing issues, and delivering expert guidance.
  • Becoming a trusted expert on OpenAI's products and platform, serving as a go-to resource for complex technical issues.
  • Serving as a critical escalation point and line of defense for complex technical issues, partnering closely with customers and Engineering teams to troubleshoot, resolve, and proactively prevent recurring problems while leveraging scripting and emerging AI capabilities to improve internal tooling and automate operational workflows
  • Taking learnings from resolving customer issues and creating our approach to scaling these solutions, partnering with Product and Go-To-Market teams.
  • Driving operational excellence by identifying opportunities for automation and AI-powered workflows, implementing scalable improvements that increase team efficiency, reducing manual effort, and elevating the overall support experience.
  • Providing occasional holiday and weekend support on call coverage, as needed, to support business and customer needs.


You might thrive in this role if you have:
  • Have 8+ years of experience in User Operations, Engineering, Support Engineering or similar technical roles, ideally within high-growth tech startups or other fast-paced environments.
  • Are comfortable using emerging technologies (ie. Codex, ChatGPT, OpenAI API, etc.) to script or engineer code (e.g., Python) for automating repetitive tasks and integrating tools.
  • Have expert-level SaaS troubleshooting skills with the ability to rapidly understand new technologies and complex concepts.
  • Polished enterprise communication and are calm with high-stakes customers during live incident calls
  • Proven experience building strong relationships with customers and cross-functional partners to drive resolution to complex issues.
  • Exceptional critical thinker and problem solver with the ability to clearly communicate complex technical issues to both customers and internal teams.
  • Thrive in ambiguity, adapt rapidly to change, continuously learn, and proactively seek opportunities for growth.
  • Bring a humble, team first mindset, a genuine eagerness to help others, and the curiosity to quickly learn whatever knowledge is needed to help both your teammates and our customers succeed.
  • Bachelor's degree in Computer Science, Computer Engineering, another relevant technical field, or equivalent practical experience.

About OpenAI

OpenAI is an artificial intelligence research laboratory consisting of the for-profit corporation OpenAI LP and its parent company, the non-profit OpenAI Inc. The company was founded in 2015 by a group of technology leaders, including Elon Musk, Sam Altman, Greg Brockman, Ilya Sutskever, and John Schulman. OpenAI's mission is to develop and promote friendly AI for the betterment of humanity. The company has developed a number of cutting-edge AI technologies, including GPT-3, a language processing system that can generate human-like text. OpenAI has received funding from a number of high-profile investors, including LinkedIn co-founder Reid Hoffman and venture capitalist Peter Thiel.
Learn more about OpenAI
Size
100 employees
Industry
Founded
2015

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