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Head of AI Strategy

Madison-Davis, LLC
York, NY Full Time
POSTED ON 6/29/2026
AVAILABLE BEFORE 9/15/2026

A leading financial services organization is seeking a Director of AI Strategy & Enablement to lead enterprise AI adoption, innovation, and delivery initiatives. This role will serve as a strategic bridge between business stakeholders, technology teams, and executive leadership, helping identify high-value opportunities for artificial intelligence while driving successful implementation and organizational adoption.


The ideal candidate combines product strategy, technology leadership, and business transformation expertise with a practical understanding of AI, machine learning, and emerging technologies. This is a highly visible leadership role focused on turning AI opportunities into measurable business outcomes.


What You'll Tackle:


  • Develop and execute an enterprise AI strategy aligned with business priorities and organizational objectives.
  • Build and maintain a prioritized roadmap for AI and automation initiatives.
  • Identify, evaluate, and prioritize high-impact AI use cases across multiple business functions.
  • Translate business needs into actionable product requirements and implementation plans.
  • Partner with engineering, architecture, data, and product teams to deliver AI-enabled solutions.
  • Support solution design, model selection, integrations, APIs, and deployment strategies.
  • Evaluate emerging AI technologies, platforms, and vendor solutions.
  • Establish governance, operating models, and best practices for AI adoption and delivery.
  • Drive organizational change management, user adoption, and AI enablement initiatives.
  • Build relationships with senior business and technology stakeholders to align AI investments with business value.
  • Support the growth and development of AI capabilities, processes, and future team structures.


What You Bring:


  • 10 years of experience across technology, product management, business transformation, consulting, engineering, or related disciplines.
  • 3 years of experience supporting AI, machine learning, generative AI, or advanced analytics initiatives.
  • Experience building, deploying, or scaling enterprise AI solutions.
  • Strong understanding of AI product lifecycle management, implementation, and adoption strategies.
  • Technical fluency across APIs, integrations, architecture, data platforms, and modern technology ecosystems.
  • Ability to influence senior stakeholders and drive cross-functional alignment.
  • Experience within financial services, investment management, asset management, or highly regulated industries.
  • Strong communication, prioritization, and leadership skills.
  • Experience leading strategic initiatives from concept through execution.
  • Ability to balance innovation, governance, risk management, and business outcomes.


Nice to Have:


  • Experience with large language models (LLMs), generative AI, prompt engineering, or AI-enabled applications.
  • Exposure to modern data platforms such as Databricks, Snowflake, Microsoft Fabric, or similar technologies.
  • Experience with cloud-native architectures, microservices, or AI integration frameworks.
  • Experience establishing AI governance, operating models, or responsible AI practices.
  • Experience building or leading emerging technology teams.
  • Exposure to investment management, capital markets, wealth management, or financial operations workflows.


What Success Looks Like:

  • Successful delivery of enterprise AI initiatives that create measurable business value.
  • Strong alignment between AI investments and strategic business priorities.
  • Increased adoption of AI-enabled capabilities across the organization.
  • Effective governance, scalability, and operationalization of AI solutions.
  • Strong collaboration across business, technology, and executive stakeholders.
  • Establishment of a sustainable foundation for long-term AI innovation and growth.

Salary : $250,000 - $300,000

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