Our New York Life culture has laid the foundation for over 180 years of commitment to our employees, agents, policy owners, and the communities where we live and work. Here you become a valued part of a welcoming, inclusive, and caring organization with a long-standing legacy in stability and growth. The strength revolves around our diversified, multi-dimensional business portfolio that goes beyond life insurance.

As a Fortune 100 company and industry leader, we provide an environment where you can explore your career ambitions, offering opportunities to tackle meaningful challenges and stretch your skills while balancing work and life priorities.  You will be part of an inclusive team guided by our belief to always be there for each other–providing the support and flexibility to grow and reach new heights while making an impact in the lives of others.

You are our future, and we commit to investing in you accordingly.

As part of Technology at New York Life, you'll have the opportunity to contribute to groundbreaking initiatives that shape our digital landscape. Leverage cutting-edge technologies like Generative AI to increase productivity, streamline processes, and create seamless experiences for clients, agents, and employees. Your expertise fuels innovation, agility, and growth — driving the company's success. 

Role Overview:  

We are seeking an innovative and strategic Head of Technical Learning and Development to drive a unified approach to learning and development across Technology, AI, and Data functions. This leader will play a critical role in enabling our multi-year tech transformation by designing and executing a future-ready learning strategy that empowers employees at all levels in a rapidly evolving digital landscape. This team will help develop, maintain, and operationalize revised role and skill architectures aligned to a modern technology workforce. By promoting continuous learning and enhancing technical expertise, they will help position Tech, Data, and AI teams for ongoing success and develop a culture of engineering excellence. Additionally, they will partner closely with HR to deliver the enterprise-wide AI learning strategy. 

What You’ll Do:  

Enable Workforce Transformation: Collaborate with the COO’s Tech AI&D Operations team to execute the strategic vision of the Tech Transformation Office (TTO), ensuring employees have the skills and capabilities needed for the future.  Drive Learning Initiatives: Lead and support critical learning programs for Tech, Data, and AI employees, and drive enterprise AI learning efforts.  Conducting Needs Assessment: Align with workforce planning process to identify skill gaps and development opportunities.  Define and Measure Success: Develop clear objectives, key results, and success metrics to track the impact of learning initiatives. 

Internal Responsibilities (Tech, Data, AI team) 

Drive a continuous learning and engineering culture in partnership with HR and TTO.  Champion and lead Career Hub engagement in Tech AI&D to support career growth.  Oversee Tech AI&D Early Career Programming and internships.  Evaluate departmental funding of independent learning programming aligned to overall strategy  Manage and optimize learning platforms and vendor relationships, including content providers and delivery platforms.  Evaluate ongoing needs and best practice around Tech, Data, and AI  

Enterprise Responsibilities 

Partner to lead AI Learning efforts across three strategic workstreams:   Ignite AI – Drive community enablement and foster knowledge sharing  Expand AI – Support enterprise tool education (e.g., Copilot, ChatGPT, etc.)  Steward AI – Support governance efforts with legal, risk, and compliance teams  Support CODA (Community of Data Analysts) through targeted learning initiatives 

What You’ll Bring:  

Bachelor's degree in a related field; advanced degree preferred.  Proven experience in determining a learner-centric strategy, executing, and leading learning and development initiatives within tech, data, and AI domains. This includes measuring effectiveness, ensuring scalability and sustainability.  Strategic thinking and ability to develop metrics and measure the success of learning programs.  Ability to curate and align learning experiences with business needs.  Strong collaboration skills with HR and other enterprise functions.  Vendor management and partnership optimization.  Excellent leadership and communication skills.  Familiarity with learning management systems and digital learning platforms. 

Preferred Skills:

Strong foundational understanding of technology, data, and AI concepts to design relevant, credible learning programs that enable meaningful engagement with technical stakeholders.   Expertise in creating adaptive, scalable learning experiences that meet the varied needs of technical employees using methods like experiential learning, labs, certifications, sandboxes, and AI-driven personalization.  Ability to drive adoption of learning initiatives through a partnership with senior leadership; building buy-in across technical teams and managing cultural change toward a continuous learning mindset.   Ability to define success metrics, build dashboards, analyze learning engagement and skills progression data, and tie learning outcomes to Tech AI&D objectives (e.g. improved technical delivery, increased velocity, and improved innovation rates).  Skill in setting, tracking, and refining objectives and key results (OKRs) that align learning initiatives to strategic technology, data, and AI goals – ensuring constant feedback loops and measurable impact on skills growth and business readiness.