Head of Technology Learning & AI Enablement Greater New York City, NY Area

The Company is seeking a Head of Technology Learning & AI Enablement to lead enterprise capability development in support of technology transformation, agile delivery, and AI adoption. Responsibilities include setting a multi-year learning strategy, building role-based agile, AI, and technical learning programs, and developing internal coaching and AI champion networks. The role will oversee learning investments and platforms, establish skills intelligence and measurement frameworks, and connect learning outcomes to business performance. It will also lead the learning and development function, promote a culture of continuous learning, and report on capability progress and emerging skills gaps. Candidates should have a bachelor’s degree in a relevant field or equivalent professional experience, at least 10 years of progressive experience in technology, learning and development, transformation, or workforce capability, and at least five years leading teams or large-scale programs. Required expertise includes learning strategy, agile delivery, technology upskilling, and workforce AI fluency, with knowledge of cloud, software engineering, data and analytics, and emerging AI technologies. Candidates should also demonstrate strong partnership and influence with senior leaders, and the ability to use learning analytics and performance metrics to assess capability growth and business impact.

Hiring Company

New York Life Insurance Company