Corporate Vice President - Head of Technology Learning & AI Enablement

New York Life • New York, NY

13h • $160,000 - $228,500 • Hybrid

About The Position

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 its transformation agenda, deliver at agile speed, and thrive in an AI-augmented environment. Working closely with the VP of Transformation and VP of Delivery, the role translates organizational strategy into measurable learning outcomes by closing capability gaps, accelerating adoption of new ways of working, and fostering continuous growth.

The role owns learning strategy across technology transformation, agile delivery, AI adoption, and technical upskilling. It governs the learning portfolio, develops enterprise curricula and role-based learning paths, builds internal coaching capacity, and establishes measurement and analytics to link learning investments to workforce capability and business outcomes.

The position leads the L&D function and promotes a culture of continuous learning, experimentation, and psychological safety. It also represents the organization externally on learning innovation, AI in L&D, and workforce capability.

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+ 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 supporting technology transformation, Agile delivery, workforce upskilling, and emerging-technology adoption.
• Strong understanding of modern technology environments, including cloud computing, software engineering, data and analytics, Agile methodologies, and emerging AI technologies, and ability to translate technical concepts into effective learning 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 use learning analytics and performance metrics to measure capability development and business impact.

Responsibilities

• Define and drive a multi-year learning and development strategy aligned with transformation, technology delivery, and AI adoption priorities.
• Translate business objectives into capability development roadmaps with milestones and success measures; represent L&D at the executive level and report progress quarterly.
• Partner with the VP of Transformation to integrate learning and change readiness into organizational transformation initiatives.
• Partner with the VP of Delivery to align curricula with delivery maturity goals and agile, iterative, outcome-driven practices.
• Govern the enterprise 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 for varied audiences.
• 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, including training and certifying enterprise coaches.
• Use delivery retrospectives and feedback loops to evolve learning programs; assess agile capability growth and correlate learning with delivery outcomes.
• Align Agile enablement with delivery OKRs and health metrics, and make capability progress visible in dashboards.
• Design and deploy an enterprise AI fluency framework with awareness, practitioner, and advanced capability tiers.
• Integrate AI literacy into transformation workstreams and pair agentic workflow adoption with targeted learning and change support.
• Create immersive agentic AI learning experiences, including sandbox environments, simulations, and cohort-based practice labs.
• Establish governance standards for AI-enabled and AI-generated learning content, including ethical-use, bias, and accuracy review processes.
• Develop and support internal AI Champions and Learning Coaches to build AI capabilities across business units.
• Track AI fluency against proficiency benchmarks and report workforce AI readiness as a workforce-planning metric.
• Own the enterprise technical skills strategy and maintain a technology skills taxonomy across priority domains.
• Design role-based technology learning paths with Engineering, Architecture, and Product leaders, based on capability gaps and future skills demand.
• Manage external learning platforms, certification providers, and academic or bootcamp partnerships.
• Lead adoption of applied learning modalities such as cloud labs, coding sandboxes, AI-powered practice tools, and simulations.
• Build skills intelligence infrastructure, including 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 use upskilling to support retention and attraction and reduce reliance on external hiring for critical technical skills.
• Define enterprise learning-success standards and own KPIs for reach and engagement, skill proficiency, business impact correlation, and program ROI.
• Build learning analytics capability and implement a 70-20-10 measurement philosophy covering formal learning, on-the-job practice, peer coaching, and experiential outcomes.
• Report quarterly to the CHRO, VP of Transformation, and VP of Delivery on capability progress, portfolio effectiveness, skills gaps, and recommended interventions.
• Build, lead, develop, and inspire a high-performing L&D team with expertise in instructional design, learning technology, performance consulting, and facilitation.
• Promote psychological safety, experimentation, learning from failure, iteration, and knowledge sharing.
• Partner with the People function to embed learning commitments in 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.

Benefits

• Full package of employee benefits, including leave programs, adoption assistance, and student loan repayment programs.
• Annual discretionary bonus eligibility.
• May be eligible to participate in an incentive program.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior