About The Job

We're looking for an experienced consulting professional to help train AI models. You'll test the newest AI models on business problems from your own practice, judge what they produce with a consultant's eye, and tell us exactly where they hold up and where they fall apart.

This is a new and quick-growing area for our company, focused on teaching AI to think like a top-tier strategy advisor. The models can already generate polished-looking slides and reports. What they can't yet do reliably is tell a sharp recommendation from a generic one. Your judgment, standards, and written rationale become the signal that shapes the next generation of AI business tools.

What You’ll Do

Write client-style briefs based on engagements you know well (a market-entry assessment, a competitive landscape, a due diligence memo, a cost-reduction plan) and run them through AI models

Review each response the way you'd review an associate's work before it reaches a partner: problem framing, structure, analytical rigor, insight, storyline, and whether it answers the client's question

Flag concrete issues, such as unsupported claims, faulty numbers, buried recommendations, or vague "AI-sounding" conclusions, and explain your reasoning

Compare responses head-to-head and pick the one you'd put in front of a leadership team

Projects Span

Strategy: market entry, growth, portfolio and competitive positioning

Market research: sizing, competitor benchmarking, customer segmentation

Leadership communications: board decks, steering committee updates,



one-pagers

Operations and transformation: process redesign, PMO, program management

Transactions: commercial due diligence, deal advisory, investment theses

Advantages Of Contracting With Us

You'll be able to choose which projects you want to work on and when

You work on your own schedule, on your own computer, from the comfort of your own home

Projects are paid hourly, up to $40-$125 USD per hour, with bonus rates available on some projects

Responsibilities

Build complete evaluation tasks: source files, a scoring rubric, and a model answer that shows what great looks like

Write clear, structured feedback that helps each new version of the model improve

Qualifications

Fluency in English (native or bilingual level)

Detail-oriented

Professional experience in management consulting, strategy, PMO, or deal advisory

Experience at a top strategy firm, Big Four advisory practice, or boutique consultancy is a strong plus

Skilled at building and critiquing work for senior stakeholders

Strong analytical and structured problem-solving skills A current, in-progress, or completed MBA or other postgraduate degree is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. Only applicants in Australia, Canada, Ireland, New Zealand, the United Kingdom, and the United States will be considered for this role. This is an independent contractor position.

#consulting

📌 Business Transformation Consultant - AI Trainer (Winnipeg)
🏢 DataAnnotation
📍 Winnipeg