SUMMARY

Location: Chicago IL
Hybrid: 3 days per week in office
The Sr. Director, Artificial Intelligence Strategist will lead enterprise-wide AI initiatives that drive innovation, operational efficiency, and sustainable growth. This role is responsible for identifying high-impact AI opportunities, overseeing implementation, and ensuring alignment with business goals. The Sr. Director will collaborate with executive leadership, portfolio companies, and technical teams to deliver measurable value while managing risk and promoting ethical AI practices. This leader will also engage with the Board of Directors to provide strategic insights and updates on AI progress and governance.

EDUCATION & EXPERIENCE

• Bachelor’s degree in Data Science, Software Engineering, Mathematics, Business, or a related field (Master’s preferred).
• 10+ years of experience in AI integration, digital transformation, or strategic technology leadership.
• Proven hands-on experience with AI technologies such as natural language processing, computer vision, and deep learning (e.g., PyTorch, TensorFlow, Hugging Face).
• Track record of leading enterprise-scale AI initiatives; experience with investment or portfolio company environments is a plus.

SKILLS & COMPETENCIES

• Deep understanding of AI/ML applications and their business impact.
• Strong executive presence with the ability to communicate complex concepts clearly and persuasively.
• Ability to influence without authority and drive change across diverse stakeholder groups.
• Analytical mindset with a focus on performance metrics and ROI.
• Proficiency in programming languages (Python, R, Java, or C++) and data visualization tools (e.g., Tableau).

• Shape Strategy: Develop and lead the enterprise AI strategy in partnership with executive leadership and advise the Board on AI trends, risks, and opportunities.
• Identify Opportunities: Pinpoint high-impact AI use cases across underwriting, asset management, operations, and portfolio companies. Evaluate proposals and guide prioritization.
• Drive Implementation: Oversee the deployment of AI tools and platforms, ensuring seamless integration, measurable outcomes, and adherence to best practices.
• Measure Impact: Define and track key performance metrics such as ROI, cost savings, and operational efficiency.
• Manage Risk: Establish governance frameworks and ensure compliance with ethical and regulatory standards in AI adoption.
• Promote Adoption: Lead internal training and advocacy efforts to build AI literacy and foster a culture of innovation.
• Lead Projects: Manage multiple AI initiatives from scoping to post-launch, aligning cross-functional teams and external partners to deliver results on time and within budget.
• Represent the Company: Serve as an AI thought leader at industry events, panels, and executive briefings.