Cloud consultant Jobs in Windsor, ON

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.

Key Responsibilities :

• Evaluate AI-generated responses to complex strategy and international business scenarios for accuracy, business judgment, analytical rigor, and executive-level clarity.
• 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.

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.
• 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.