VP AI Investing | Scrabble & Jigsaw

Posted on August 27, 2025

Job Description

Vice President – Investments (Artificial Intelligence)  We are seeking a seasoned investment professional (8–10 years of experience) with deep expertise in evaluating, structuring, and managing private equity investments, with a strong focus on the Artificial Intelligence (AI) sector. The ideal candidate will combine rigorous financial acumen with an understanding of AI technologies, business models, and regulatory considerations shaping this rapidly evolving industry.  What will you be doing?  ● Deal Sourcing & Evaluation: Assess potential AI-focused private equity opportunities by analyzing financial performance, scalability of AI models, data infrastructure, IP defensibility, competitive positioning, and sector-specific regulatory risks.  ● Financial & Business Modeling: Build and evaluate financial models that capture the unique economics of AI businesses, including R&D intensity, compute costs, recurring vs. project-based revenues, and scalability of deployment.  ● Market & Technology Analysis: Evaluate AI industry trends, product-market fit, and adoption risks across verticals (healthcare, fintech, enterprise SaaS, consumer, etc.) to assess long-term growth potential.  ● Deal Structuring: Assist in structuring transactions, negotiating terms, pricing, and drafting investment agreements tailored to AI ventures.  ● Due Diligence: Lead cross-functional diligence across technical, financial, legal, and regulatory dimensions—ensuring compliance with AI ethics, data protection laws, and emerging policy frameworks.  ● Portfolio Support: Post-investment, monitor portfolio companies’ performance and help management teams scale responsibly, balancing financial returns with responsible AI deployment.  ● Thesis Development: Build and refine the firm’s AI investment thesis by identifying sub-sectors, emerging technologies, and market dynamics that align with long-term investment opportunities.