Salary:

CAD $110,000–$120,000 per year

About the Role We are seeking an

AI Support Analyst – Level 2.5

to provide frontline end-user support across the firm's AI product portfolio.

The role involves answering user questions, troubleshooting common and intermediate issues, documenting queries and resolutions, and escalating complex technical issues to Level 3 engineering teams.

The AI portfolio includes

Microsoft Copilot, OpenAI ChatGPT, Anthropic Claude, Grok, Google Gemini , and other AI products introduced to the organization, such as Zoom AI Companion.

Each analyst will maintain working knowledge of the full AI portfolio while serving as the primary point of contact for one assigned AI product.

Key Responsibilities

Respond to end-user questions across helpdesk tickets, support channels, email, and direct queries for the full AI product portfolio.

Troubleshoot and resolve common and intermediate AI-related issues at first contact.

Escalate complex engineering issues to Level 3 teams with clear and complete technical context.

Document every user query, troubleshooting step, and resolution in a structured format.

Build and maintain a knowledge base to support the development of a future AI support agent.

Assist Level 3 engineering teams and QA testers by reproducing issues, gathering evidence, and validating fixes.

Own one AI product as the primary point of contact while maintaining working knowledge of all supported AI products.

Provide support coverage for the partner location.

Maintain and improve self-help content, FAQs, and end-user guidance.

Ensure smooth handover of open issues between locations during shift changes.

Required Skills & Qualifications

Experience in

technical support, service desk, or application support

within an enterprise setting.





Familiarity with

Microsoft 365 (M365)

and a strong interest in AI products.

Ability to quickly learn new AI tools, products, and features.

Experience with ticketing and knowledge management tools, such as:

ServiceNow

Jira

Confluence

Strong verbal and written communication skills.

Excellent customer-facing troubleshooting and user-support skills.

Experience reading and writing technical documentation.

Ability to document queries and resolutions in a structured and consistent manner.

Strong collaboration, knowledge-sharing, and mentoring skills.

Core Skills

AI Product Support

Level 2 / Level 2.5 Technical Support

Application Support

Microsoft 365

OpenAI ChatGPT

Anthropic Claude

Grok

Google Gemini

Zoom AI Companion

ServiceNow

Technical Troubleshooting

Issue Triage and Escalation

Knowledge Management

Technical Documentation

QA Support and Issue Reproduction

ITIL Processes

Cross-location Support and Handover

Preferred Qualifications

Experience supporting

banking or financial services environments .

Experience mentoring teammates and colleagues.

Strong knowledge-sharing and team-development practices.

Understanding of ITIL processes and structured escalation procedures.

For candidates based in Montreal,

English/French bilingual communication is an asset .

Ideal Candidate Profile We are looking for a customer-focused technical support professional who can troubleshoot enterprise AI products, communicate effectively with end users, maintain accurate support documentation, and coordinate with engineering and QA teams.

Candidates with enterprise service desk, application support, Microsoft 365, ServiceNow, Jira, and knowledge management experience are encouraged to apply.

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📌 AI Support Analyst – Level 2.5 (Winnipeg)
🏢 PeoplePilot
📍 Winnipeg