Corporate Vice President - Head of Technology Learning & Development

New York Life•New York, NY

9d•$160,000 - $228,500•Hybrid

About The Position

The Head of Technology Learning & Development provides strategic leadership for enterprise-wide technology capability building. The role ensures the organization develops the skills, mindsets, and practices needed to execute its transformation agenda, deliver at an agile speed, and thrive in an AI-augmented environment. In partnership with the VP of Tech Strategy Execution, the VP of Delivery CoE, and the enterprise L&D CoE, the role translates technology and delivery strategy into measurable learning outcomes, closes capability gaps, accelerates adoption of new ways of working, and builds a culture of continuous growth. The position leads technology learning strategy and portfolio governance; develops Agile, AI fluency, and technical upskilling programs; and establishes measurement approaches that connect learning investment to proficiency gains and business outcomes. It also builds and leads a technology learning team, advocates for continuous learning across the technology organization, and represents the organization on learning technology innovation, AI in L&D, and workforce capability. The role is based in a hybrid work arrangement requiring three days per week at the designated work location. The position is exempt, discretionary bonus eligible, and has a stated salary range of $160,000–$228,500.

Requirements

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

Responsibilities

Define and drive a multi-year technology learning and development strategy aligned with enterprise learning strategy and priorities across transformation, technology delivery, and AI.
Translate technology objectives into capability development roadmaps with milestones and success measures, and report quarterly on capability progress.
Partner with the VP of Tech Strategy Execution to embed learning and change-readiness programs alongside transformation initiatives.
Partner with the VP of Delivery CoE to align curricula with delivery maturity goals and agile, iterative, outcome-driven practices.
Govern the technology L&D portfolio, including investment prioritization, vendor and platform strategy, and build-versus-buy decisions.
Design, scale, and evolve an enterprise Agile learning curriculum covering Scrum, Kanban, SAFe, and iterative delivery practices.
Develop role-based Agile learning paths for Product Owners, Scrum Masters, Delivery Leads, Technical Leads, and Business Stakeholders.
Build internal Agile coaching and facilitation capacity, and establish feedback loops between delivery retrospectives and L&D design.
Create frameworks to assess Agile capability growth and relate learning participation to delivery velocity, quality, and predictability.
Lead enterprise deployment of a digital and AI fluency framework, contributing technology-specific content across awareness, practitioner, and advanced tiers.
Integrate AI literacy into transformation workstreams and develop immersive learning experiences such as sandbox environments, live-use-case simulations, and practice labs.
Contribute to governance standards for AI-enabled and AI-generated learning content, including ethical use, bias and accuracy review, and deployment frameworks.
Partner with enterprise L&D to enable an AI Champions network and track AI fluency and workforce AI readiness.
Own the technical skills strategy for the technology workforce and maintain the technology domain skills taxonomy with enterprise L&D and HR.
Design role-based technology learning paths with Engineering, Architecture, and Product leadership, mapped to capability gaps and future skills demand.
Manage external technology learning platforms, certification providers, and academic or bootcamp partnerships.
Lead adoption of applied technical learning modalities, including cloud labs, coding sandboxes, AI-powered practice tools, and simulations.
Partner with HR and enterprise L&D on skills proficiency mapping, gap analysis, dashboards, and longitudinal tracking to inform workforce planning, internal mobility, and succession.
Partner with Talent Acquisition and HR Business Partners to position L&D upskilling as a retention and attraction lever.
Define learning success standards and own KPIs for reach and engagement, proficiency progression, business impact correlation, and program ROI.
Build learning analytics capability and implement a 70-20-10 measurement philosophy that includes formal learning, on-the-job practice, peer coaching, and experiential outcomes.
Report quarterly to the CHRO, VP of Tech Strategy Execution, and VP of Delivery CoE on capability progress, portfolio effectiveness, emerging skills gaps, and recommended interventions.
Build, lead, develop, and inspire a high-performing technology learning team with expertise in instructional design, learning technology, performance consulting, and facilitation.
Foster psychological safety and experimentation, and champion continuous learning in performance frameworks, leadership competencies, and talent reviews.
Represent the technology organization at industry forums and with vendor partners as a thought leader on learning technology innovation, AI in L&D, and workforce capability.