Strategy Consultant / Sr Strategy Consultant – Remote

YO IT Consulting; Toronto; Remote; CAD 90,000 - 120,000; Full time

Job summary

YO IT Consulting is seeking a senior strategy consultant who excels in ambiguous problem-solving and market analysis. The role involves evaluating AI systems' reasoning related to international business strategy, providing insights to strengthen model accuracy, and ensuring executive-level clarity.

The ideal candidate will have 4+ years of experience in strategy consulting, demonstrating strong analytical capabilities and hands-on experience with senior stakeholders. This is a unique opportunity for professionals who wish to impact the AI landscape.

Qualifications

• 4+ years of professional experience in strategy consulting or a related field.
• Hands-on experience developing strategy recommendations for senior stakeholders.
• Deep knowledge of strategy frameworks and international expansion strategy.
• Experience structuring ambiguous business problems and translating insights.

Responsibilities

• Evaluate AI-generated responses for accuracy and analytical rigor.
• Support benchmarking efforts against expert-level expectations.
• Review AI-generated content for sound strategy practices.
• Shape AI communication standards for strategy-related content.

Skills

Strategy consulting frameworks

Market analysis

Competitive positioning

Business model evaluation

Global markets understanding

Cross-border business dynamics

Job description

Overview

Job Type: Contractor

Location: Remote

Role Description

If you’re a senior strategy consultant who thrives on ambiguity, structured problem-solving, market analysis, and executive-level decision-making, this is a unique opportunity to contribute directly to how the next generation of AI systems reason through complex business and international strategy challenges. We’re looking for experienced strategy professionals who understand market entry, competitive positioning, and operating model design. You’ll challenge advanced language models on strategy consulting and international strategy topics, to strengthen model reasoning, accuracy, and judgment.

Your Profile

• 4+ years of professional experience in strategy consulting, international strategy, corporate strategy, market entry, growth strategy, commercial due diligence, or a closely related field.
• Significant hands-on experience developing strategy recommendations for senior stakeholders, including executive teams, boards, investors, or public-sector decision-makers.
• Deep knowledge of strategy consulting frameworks, market analysis, competitive positioning, business model evaluation, and international expansion strategy.
• Strong understanding of global markets, cross-border business dynamics, geopolitical and regulatory risk, operating models, and strategic tradeoffs.
• Proven experience structuring ambiguous business problems, developing hypotheses, analyzing complex information, and translating insights into practical recommendations.
• Demonstrated experience in creating client-ready deliverables such as strategy decks, executive memos, market assessments, transformation roadmaps, or investment recommendations.
• Previous experience with AI data training, annotation, or evaluating AI-generated technical content is a strong plus.

Key Responsibilities

• Evaluate AI-generated responses to complex strategy and international business scenarios for accuracy, business judgment, analytical rigor, and executive-level clarity.
• Support benchmarking efforts by comparing model responses against expert-level expectations for strategy consulting deliverables, case interviews, executive memos, and board presentations.
• Review and refine AI-generated prompts, case analyses, recommendations, frameworks, and responses to ensure they reflect sound strategy consulting practices.
• Shape AI communication standards for strategy-related content, ensuring outputs are concise, structured, commercially grounded, and appropriate for senior business audiences.
• Help improve how AI systems reason through international strategy questions involving regulatory environments, cultural context, macroeconomic conditions, supply chains, and geopolitical complexity.