VP / Chief Learning Officer (CLO)

New York Life•New York, NY

21h•Hybrid

About The Position

The Chief Learning Officer (CLO) will bring a strong, forward-looking point of view on the future of work leveraging AI not only to build skills across the enterprise and within the function, but to fundamentally reshape how learning is designed, created, and delivered. This includes reimagining learning as a more experiential, personalized, and embedded capability, moving beyond traditional programs to dynamic experiences that drive real behavior change. In addition, the CLO will lead the enterprise skills strategy, overseeing the development and integration of a comprehensive skills ecosystem—including Career Hub, Eightfold, upskilling and reskilling initiatives, and job architecture—to enable a future-ready, skills-driven organization. The CLO will set the enterprise learning strategy and agenda across all levels of the organization, including employees, managers, leaders, and high-potential talent, ensuring a cohesive and aligned approach to capability building. They will lead the transformation of learning at New York Life from a programmatic function to a strategic driver of enterprise capability, performance, and how the organization evolves how work gets done. This role is central to shaping a more adaptive, skills-driven organization, redefining how capabilities are built over time. A critical component of this work is enabling leaders to drive this evolution by building capability, modeling new ways of working, and accelerating adoption of AI across the enterprise. Reporting to the SVP, Talent Management, this leader operates at the intersection of business strategy, talent, and technology, with accountability for building a modern, AI-enabled capability ecosystem and advancing innovative learning experiences that drive measurable impact.

Requirements

Proven ability to transform learning into a strategic driver of enterprise capability and business performance
Strong, forward-looking perspective on the future of work, including how AI reshapes skills, roles, and how learning is created and delivered
Experience leading enterprise-wide skills or workforce transformations
Track record of driving measurable behavior change and impact at scale
Ability to operate at the intersection of business strategy, talent, and technology
Strong orientation toward learning innovation and experience design, with the ability to create engaging, high-impact experiences that drive real behavior change
Data-driven mindset, with the ability to define meaningful success metrics and use insights to continuously improve learning outcomes and investment decisions
Ability to simplify and focus, translating broad enterprise priorities into a clear, actionable learning agenda
Strong executive presence with the ability to influence, challenge, and align senior leaders
Experience building high-performing teams and managing strategic vendor and technology partnerships
Strong, forward-looking perspective on the future of work, including how AI and skills-based models reshape roles, career pathways, and how learning is created and delivered

Responsibilities

Define and drive the enterprise capability and skills strategy aligned to business priorities and future work needs
Activate priority groups through focused, role-based upskilling and reskilling (e.g., academies, use-case-driven learning, immersive experiences)
Translate enterprise priorities into a clear, focused set of critical capabilities, and ensure they are brought to life across the enterprise through integrated, high-impact learning experiences that extend beyond self-paced content into how work is performed
Establish capability building as a core engine of performance and a fundamental expectation of all roles—embedding learning into the flow of work and reinforcing a culture where continuous development is expected, applied, and sustained at scale
Leverage data to prioritize investments, scale what works, and stop what doesn’t
Support the enterprise AI upskilling agenda and broader skills strategy by translating enterprise AI need and priorities into focused, persona-based capability building approaches and identifying scalable, engaging content that drives true adoption
Embed AI capability building into how work gets done—ensuring learning is applied, reinforced, and sustained over time, not delivered as one-time interventions
Lead the design and integration of the enterprise skills ecosystem, aligning platforms and initiatives (e.g., Career Hub, Eightfold), job architecture, and upskilling/reskilling efforts into a unified strategy that enables talent mobility, workforce planning, and a future-ready, skills-driven organization
Own and evolve the enterprise leadership and manager development strategy, including the continued build-out and sustainment of our flagship program Lead Forward as a multi-year journey for all Leaders. Ensure program is directly aligned to enterprise priorities and drives the behaviors required to evolve how the organization operates.
Build out evolved approach to top talent and HiPo programs across enterprise to ensure we are focused on readying future leaders across NYL and building bench strength through talent
Integrate coaching (human and AI-enabled) into daily leadership and team effectiveness
Continuously assess impact and evolve the approach to ensure leadership and manager development translates into measurable changes in behavior and performance across NYL
Design and scale an AI-enabled learning ecosystem that embeds learning, coaching, and development into the flow of work
Leverage AI and cutting-edge technology to personalize development, accelerate skill acquisition, and enable real-time performance support
Drive innovation in how learning is created and delivered across the team with a focus on experience, using AI to design, curate, and scale high-impact experiences and leveraging AI tools, such as Sana, to its best ability
Partner closely with Technology and vendors to continue to optimize, evolve and integrate platforms, tools, and roadmaps aligned to enterprise priorities
Own vendor and partnership performance across the learning ecosystem, with clear accountability for value realization. Actively manage relationships, holding partners accountable and challenging performance where outcomes are not meeting expectations
Use data and governance to continuously optimize programs and investments
Define dashboards and metrics that truly help to assess and measure success of our teams work, not just NPS, usage or hours of learning consumed, but including more nuanced elements such as capability growth, behavior change, and business outcomes
Build and lead a high-performing, future-ready learning team with strong capabilities in consulting, experience design, data, and technology
Set a clear vision and strategy for the function, fostering a culture of innovation, accountability, and continuous improvement aligned to enterprise priorities
Coach, develop, and inspire the team, ensuring individuals are growing their skills and evolving alongside advancements in AI, technology, and modern learning practices
Continuously upskill the function, building leading-edge capabilities in AI-enabled learning, experience design, and data-driven decision making
Establish high standards of excellence, ensuring the team delivers best-in-class, high-impact solutions that drive measurable business outcomes
Create an environment that encourages experimentation and learning, while maintaining discipline around prioritization, quality, and impact