Corporate Vice President - Head of Technology Learning & Development

Location Designation: Hybrid - 3 days per week 

Technology, Data, AI and Ventures:

Within the Tech, Data, AI, Ventures (TDAV) organization, our work is guided by a shared vision: deploying the power of technology, data, AI and ventures to accelerate sustainable competitive advantage for New York Life's businesses. We build solutions that power how we serve policy owners, agents, advisors and employees while delivering measurable business outcomes.

Across technology, data, AI, cyber, product, digital experience, architecture and infrastructure, TDAV combines the scale and investment of an industry leader, access to leading-edge technologies and the opportunity to help shape how a world-class financial services company competes in the AI era - all backed by the stability and purpose of a mutual company built to last.

Purpose of the Role

The Head of Technology Learning & Development provides strategic leadership for enterprise-wide technology capability building, ensuring the organization develops the skills, mindsets, and practices needed to execute on its transformation agenda, deliver at an agile speed, and thrive in an AI-augmented environment.

Working in close partnership with the VP of Tech Strategy Execution and the VP of Delivery CoE, this role translates technology and delivery strategy into measurable learning technology outcomes - closing capability gaps, accelerating adoption of new ways of working, and building a culture of continuous growth.

Key Responsibilities

1. Strategic Technology Learning Leadership

Define and drive a multi-year technology learning and development strategy, aligned to the enterprise learning strategy and to organizational priorities across Transformation, Technology Delivery, and AI.

• Serve as the enterprise authority on technology learning strategy, translating technology objectives into capability development roadmaps with clear milestones and success measures.
• Partner with the VP of Tech Strategy Execution to embed learning as a core lever of organizational change, ensuring change-readiness programs are designed alongside—not after—transformation initiatives.
• Partner with the VP of Delivery CoE to align curricula with delivery maturity goals, ensuring learning enables teams to adopt agile, iterative, and outcome-driven delivery practices in real time.
• Govern the technology L&D portfolio: investment prioritization, vendor/platform strategy, and build-vs-buy decisions for technology capability development,  coordinating with the enterprise L&D CoE.
• Represent technology learning at the executive level, reporting on capability progress against transformation and delivery priorities on a quarterly basis.

2. Agile Capability Development

In Partnership with the VP of Delivery CoE

Design, scale, and continuously evolve an enterprise-wide Agile learning curriculum that enables teams at every level to deliver with speed, discipline, and customer-centricity.

• Build a tiered Agile curriculum spanning Scrum, Kanban, SAFe (Scaled Agile Framework), and iterative delivery practices—tailored to functional, cross-functional, and leadership audiences.
• Develop role-based learning paths in collaboration with the VP of Delivery CoE for Product Owners, Scrum Masters, Delivery Leads, Technical Leads, and Business Stakeholders.
• Build internal Agile coaching and facilitation capacity, training and certifying a cadre of enterprise coaches who embed agile mindsets at the team and program level.
• Establish closed feedback loops between delivery retrospectives and L&D design—ensuring the learning portfolio continuously evolves with delivery maturity and real-world team challenges.
• Create assessment frameworks to measure agile capability growth and correlate learning participation with delivery velocity, quality, and predictability outcomes.
• Align L&D Agile enablement with the VP of Delivery CoE's OKRs and delivery health metrics, making capability progress visible in delivery dashboards.

3. Agentic AI & AI Fluency

In Partnership with the VP of Tech Strategy Execution and the Enterprise L&D CoE

Lead the design and enterprise-wide deployment on digital and AI fluency framework that equips every employee—from frontline contributors to senior leaders—with the knowledge, confidence, and practical skills to work effectively alongside AI systems and agentic tools.

• Contribute SME thought leadership and technology-specific content to the enterprise AI fluency taxonomy with three capability tiers:
• Awareness: Foundational AI literacy for all employees (enterprise-led).
• Practitioner: Applied AI and prompt engineering for operational roles.
• Advanced: Agentic workflow design, AI governance, and AI-human teaming for technical and leadership roles.
• Partner with the VP of Tech Strategy Exeuction to integrate AI literacy into all active transformation workstreams—ensuring adoption of agentic workflows is always paired with targeted, just-in-time learning and structured change support.
• Design and deploy immersive agentic AI learning experiences—including sandbox environments, live use-case simulations, and cohort-based practice labs—that build real-world competency, not just theoretical awareness.
• Contribute to enterprise governance standards for AI-enabled and AI-generated  learning content, including ethical use guidelines, bias and accuracy review processes, and frameworks for when and how agentic learning tools are deployed.
• Partner with the enterprise L&D team on enabling enterprise AI Champions network, to develop and support AI Champions and Learning Coaches who drive peer-to-peer AI capability building at scale across business units.
• Track AI fluency progression across the organization using defined proficiency benchmarks and report on workforce AI readiness as a strategic workforce planning metric.

4. Technology Learning & Upskilling

Own the technical skills strategy for the technology workforce, ensuring the workforce continuously builds the technology capabilities required to support current delivery and future innovation priorities.

• Maintain and govern the technology domain skills taxonomy, as part of the enterprise skills initiative taxonomy with the enterprise L&D CoE and HR, covering priority domains: cloud computing, data & analytics, DevOps/platform engineering, cybersecurity, AI/ML engineering, and modern software delivery practices.
• Design role-based technology learning paths in partnership with Engineering, Architecture, and Product leadership—mapped to current capability gaps and future skills demand derived from workforce and technology roadmaps.
• Manage a strategic ecosystem of external technology learning platforms, technology certification providers, and academic or bootcamp partners to accelerate technology upskilling at scale without solely relying on build.
• Lead adoption of immersive and applied learning modalities for technical training—including cloud labs, coding sandboxes, AI-powered practice tools, and simulation environments—to improve learning transfer and real-world application.
• Partner with HR and the enterprise L&D CoE, who lead the enterprise skills intelligence infrastructure, to provide technology skills taxonomy, proficiency  mapping, gap analysis dashboards, and longitudinal tracking—to inform technology workforce planning, internal mobility, and succession decisions.
• Partner with Talent Acquisition and HR Business Partners to position L&D upskilling as a retention and attraction lever, reducing dependency on external hiring for critical technical skills.

5. Learning Effectiveness & Measurement

Define the standards by which learning success is measured across the enterprise, ensuring L&D investment is demonstrably linked to business outcomes.

• Own KPIs spanning four dimensions:
• Learning Reach & Engagement
• Skill Proficiency Progression
• Business Impact Correlation: Linked to delivery, transformation, and AI adoption metrics.
• Program ROI
• Build a learning analytics capability that generates actionable insights from learner data, enabling continuous improvement of program design, content, and delivery modality.
• Implement a 70-20-10 measurement philosophy—quantifying not just formal learning completions, but applied practice on the job, peer coaching, and experiential learning outcomes.
• Report quarterly to the CHRO, VP of Tech Strategy Execution, and VP of Delivery CoE on capability progress, portfolio effectiveness, and emerging skills gaps with recommended interventions, with visibility and alignment to the CHRO and enterprise L&D leadership.

6. Organizational Leadership & Culture

Build and lead a high-performing technology  learning team and serve as an enterprise advocate within the technology organization for a culture where learning is continuous, deliberate, and embedded in the flow of work.

• Lead, develop, and inspire a technology learning team with expertise spanning modern instructional design, learning technology, performance consulting, and facilitation—organized to support enterprise technology training needs at speed, partnering and drawing on the enterprise L&D CoE's shared expertise and services.
• Foster a culture of psychological safety and experimentation where learning from failure, iterating on approaches, and sharing knowledge are actively rewarded.
• Champion continuous learning as a leadership behavior—partnering with the HR function and the enterprise L&D CoE to embed learning commitments into performance frameworks, leadership competencies, and talent reviews.
• Serve as an external thought leader and enterprise spokesperson on learning technology innovation, AI in L&D, and workforce capability—representing the technology organization at industry forums, with vendor partners, and in talent market positioning.

Basic Qualifications