Corporate Vice President - Head of Technology Learning & AI Enablement

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.

Head of Technology Learning & AI Enablement

Purpose of the Role

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

Working in close partnership with the VP of Transformation and the VP of Delivery, this role translates organizational strategy into measurable learning outcomes—closing capability gaps, accelerating adoption of new ways of working, and building a culture of continuous growth.

Key Responsibilities

1. Strategic Learning Leadership

Define and drive a multi-year L&D strategy directly aligned to organizational priorities across Transformation, Technology Delivery, and AI adoption.

- Serve as the enterprise authority on learning strategy, translating business objectives into capability development roadmaps with clear milestones and success measures.
- Partner with the VP of Transformation 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 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 enterprise L&D portfolio: investment prioritization, vendor/platform strategy, and build-vs-buy decisions for capability development.
- Represent L&D 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

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 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's OKRs and delivery health metrics, making capability progress visible in delivery dashboards.

3. Agentic AI & AI Fluency

In Partnership with the VP of Transformation

Lead the design and enterprise-wide deployment of an 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.

- Define an AI fluency taxonomy with three capability tiers:

Awareness: Foundational AI literacy for all employees.
- 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 Transformation 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.
- Establish 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.
- Identify, develop, and support a network of internal 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 enterprise technical skills strategy, ensuring the workforce continuously builds the technology capabilities required to support current delivery and future innovation priorities.

- Maintain and govern an enterprise technology skills taxonomy 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 learning platforms, technology certification providers, and academic or bootcamp partners to accelerate upskilling at enterprise scale without solely relying on build.
- Lead adoption of immersive and applied learning modalities—including cloud labs, coding sandboxes, AI-powered practice tools, and simulation environments—to improve learning transfer and real-world application.
- Build a skills intelligence infrastructure: skills taxonomy, proficiency mapping, gap analysis dashboards, and longitudinal tracking—to inform 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 L&D 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 Transformation, and VP of Delivery on capability progress, portfolio effectiveness, and emerging skills gaps with recommended interventions.

6. Organizational Leadership & Culture

Build and lead a high-performing L&D function and serve as an enterprise advocate for a culture where learning is continuous, deliberate, and embedded in the flow of work.

- Lead, develop, and inspire an L&D team with expertise spanning modern instructional design, learning technology, performance consulting, and facilitation—organized to support the enterprise at speed.
- 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 People function to embed learning commitments into performance frameworks, leadership competencies, and talent reviews.
- Serve as an external thought leader and enterprise spokesperson on learning innovation, AI in L&D, and workforce capability—representing the organization at industry forums, with vendor partners, and in talent market positioning.

Basic Qualifications

- Bachelor's degree in Computer Science, Information Technology, Engineering, Human Resources, Organizational Development, Business Administration, or a related field, or equivalent professional experience.
- 10+ years of progressive experience in technology, learning and development, enterprise transformation, or workforce capability development, including experience supporting technology-driven organizations.
- 5+ years of experience leading teams, enterprise learning programs, or large-scale technology capability development and transformation initiatives.
- Demonstrated experience developing and executing learning and capability development strategies that support technology transformation, Agile delivery practices, workforce upskilling, and adoption of emerging technologies.
- Strong understanding of modern technology environments, including cloud computing, software engineering, data and analytics, Agile methodologies, and emerging AI technologies, with the ability to translate technical concepts into effective learning and development programs.
- Demonstrated experience driving workforce AI fluency and adoption initiatives, with an understanding of generative AI, agentic AI capabilities, AI-enabled workflows, and their application to enterprise transformation and workforce development.
- Proven ability to partner with senior technology and business leaders, influence cross-functional stakeholders, and leverage learning analytics and performance metrics to measure capability development and business impact.

Job Level: LEVELMG3

Pay Transparency

Salary Range: $160,000-$228,500

Overtime eligible: Exempt

Discretionary bonus eligible: Yes

Sales bonus eligible: No

Actual base salary will be determined based on several factors but not limited to individual’s experience, skills, qualifications, and job location. Additionally, employees are eligible for an annual discretionary bonus. In addition to base salary, employees may also be eligible to participate in an incentive program.

Company Overview

At New York Life, our 180-year legacy of purpose and integrity fuels our future. As we evolve into a more technology-, data-, and AI-enabled organization, we remain grounded in the values that drive lasting impact.

Our diverse business portfolio creates opportunities to make a difference across industries and communities—inviting bold thinking, collaborative problem-solving, and purpose-driven innovation. Here, you’ll find the rare balance of long-standing stability and forward momentum, supported by an inclusive team that honors tradition while embracing progress.

As a Fortune 100 mutual company, we offer a place to grow your skills, contribute to meaningful work, and deliver solutions that matter. Your ideas drive what’s next, and your growth powers it.

Our Benefits

We provide a full package of benefits for employees – and have unique offerings for a modern workforce, including leave programs, adoption assistance, and student loan repayment programs. Based on feedback from our employees, we continue to refine and add benefits to our offering, so that you can flourish both inside and outside of work. Click here to discover more about our comprehensive benefit options or visit our NYL Benefits Site .

Our Commitment to Inclusion

At New York Life, fostering an inclusive workplace is fundamental to who we are and how we serve our communities. We have a longstanding commitment to creating an environment where individuals can contribute their best and succeed together. This foundation is rooted in our core values of humanity and integrity, ensuring that every employee feels valued and supported. By embracing a broad range of perspectives and experiences, we achieve greater success and fulfill our promise of providing financial security and peace of mind to families across all communities.  Click here to learn more about New York Life’s leadership in this space.​

Recognized as one of Fortune’s World’s Most Admired Companies, New York Life is committed to improving local communities through a culture of employee giving and volunteerism, supported by the  Foundation . We're proud that due to our mutuality, we operate in the best interests of our policy owners. To learn more about career opportunities at New York Life, please visit the Careers page of www.NewYorkLife.com .

Job Requisition ID: 95216