Strategy & Operations Manager - AI Trainer

DataAnnotation; Montreal; Remote; CAD 145,000 - 241,000; Full time

Job summary

DataAnnotation is seeking an experienced Management Consultant to train AI models on real business problems and judge outputs with a consultant’s eye. You’ll write client-style briefs and test model reasoning against high standards of rigor and clarity.

You will review AI-generated outputs for problem framing, structure, and substantiation, ensuring recommendations are concrete and tailored to client needs.

Qualifications

• Fluency in English (native or bilingual) and 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.

Responsibilities

• Write client-style briefs from engagements you know well and run them through AI models.
• Review each response like an associate’s work before it reaches a partner: problem framing, structure, rigor, insight, and storyline.
• Flag concrete issues such as unsupported claims 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.

Skills

Strategy

Market research

Leadership communications

PMO

Deal advisory

Education

MBA or equivalent

Job description

We’re looking for an experienced Management Consultant to help train AI models. You’ll test the newest 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 fast-growing area, 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 actually do

• Write client-style briefs from 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 like 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.

Problems draw on whatever you know best:

• Strategy: market entry, growth, portfolio, and competitive positioning.
• Market research: sizing, competitor benchmarking, and customer segmentation.
• Leadership communications: board decks, steering-committee updates, and one-pagers.
• Operations and transformation: process redesign, PMO, and program management.
• Transactions: commercial due diligence, deal advisory, and investment theses.

Roles this fits

Common backgrounds: Strategy Consultant, Management Consultant, Deal Advisory Consultant.

What we look for

• Fluency in English (native or bilingual level).
• 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.
• Only applicants based in Australia, Canada, Ireland, New Zealand, the United Kingdom, or the United States will be considered for this role.

Compensation

Up to $125+/hr depending on task difficulty and specialization. Many contributors add $100k–$200k a year; some make it their full-time income.

About DataAnnotation

DataAnnotation is where 1M+ experts train the world’s leading AI models. Hundreds of millions paid to contributors to date, and the average contributor stays 5+ years. Flexible, remote, and always project-available.