AI Support Engineer – Weekend Shift

OpenAI

. Work directly with customers through support tickets and live calls .

Posted 9/29/2026full-timeRemote • CanadaSeniorLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expert-level SaaS troubleshooting skills and the ability to communicate complex technical issues effectively. Proven experience in user operations and support engineering, with a focus on leveraging emerging technologies like OpenAI API and Python to enhance operational workflows.

Highest-signal resume keywords

SaaS TroubleshootingOpenAI APIPython ScriptingCustomer Relationship ManagementCritical Thinking

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Technical SupportAPI TroubleshootingIntegration ChallengesAuthentication ErrorsDebuggingSystem AnalysisAutomationEmerging TechnologiesOperational WorkflowsIncident Management

Soft Skills

Enterprise CommunicationProblem-SolvingRelationship BuildingAdaptabilityTeam Collaboration

Tools & Technologies

OpenAI ProductsCodexChatGPT

Certifications & Qualifications

Bachelor’s Degree in Computer ScienceBachelor’s Degree in Computer Engineering

Industry Keywords

User OperationsSupport EngineeringHigh-Growth Tech StartupsFast-Paced Environments

Tech Stack

Tools & technologies

PythonGo

About the role

Key responsibilities & impact

Work directly with customers through support tickets and live calls
Troubleshoot and resolve complex technical issues, including API failures, integration challenges, authentication errors, and production incidents
Provide end-to-end ownership through debugging logs, analyzing system behavior, reproducing issues, and delivering expert guidance
Become a trusted expert and go-to resource on OpenAI’s products and platform
Serve as a critical escalation point and line of defense for complex technical issues
Partner with customers and Engineering teams to troubleshoot, resolve, and proactively prevent recurring problems
Use scripting and emerging AI capabilities to improve internal tooling and automate operational workflows
Capture learnings from customer issue resolution and help scale solutions with Product and Go-To-Market teams
Identify automation and AI-powered workflow opportunities and implement scalable improvements
Reduce manual effort and elevate the overall support experience
Provide occasional holiday and weekend on-call support as needed

Requirements

What you’ll need

8+ years of experience in User Operations, Engineering, Support Engineering, or similar technical roles
Experience ideally within high-growth tech startups or other fast-paced environments
Comfortable using emerging technologies such as Codex, ChatGPT, and OpenAI API to script or engineer code, e.g. Python
Expert-level SaaS troubleshooting skills
Ability to rapidly understand new technologies and complex concepts
Polished enterprise communication
Ability to remain calm with high-stakes customers during live incident calls
Proven experience building strong relationships with customers and cross-functional partners to resolve complex issues
Exceptional critical thinking and problem-solving skills
Ability to clearly communicate complex technical issues to customers and internal teams
Ability to thrive in ambiguity, adapt rapidly to change, continuously learn, and seek growth opportunities
Humble, team-first mindset and eagerness to help teammates and customers
Bachelor’s degree in Computer Science, Computer Engineering, another relevant technical field, or equivalent practical experience
Ability to work a standard 5x8 work week with one day covering weekend shifts each week
Authorization to work in Canada

Benefits

Comp & perks

Occasional holiday and weekend support on-call coverage, as needed
Reasonable accommodations for applicants with disabilities
Immigration and sponsorship support may be provided based on individual circumstances