Director, Learning & Development - AI Upskilling & Reskilling

Mastercard•Town/Village of Harrison, NY

About The Position

At Mastercard, the rapid acceleration of AI, automation, and emerging technologies is fundamentally reshaping how work gets done—and what skills matter most. The Director of AI Upskilling & Reskilling plays a critical enterprise role in ensuring our workforce is equipped to thrive in this transformation. Reporting to the Vice President, Skill Acceleration, this role is accountable for owning and delivering Mastercard’s enterprise-wide AI upskilling strategy and curriculum, as well as designing and implementing reskilling and redeployment pathways that enable workforce agility, productivity, and internal mobility at scale. This leader brings a strong, practical point of view on AI capability-building—translating complex and fast-evolving technologies into clear, role-relevant, and business-applied learning experiences. The Director is both a strategic thought leader and an execution-oriented builder, with proven ability to move beyond theory into real-world application that drives measurable business outcomes.

Requirements

Extensive experience in learning, talent, workforce transformation, or related leadership roles, with demonstrated ownership of large-scale, enterprise initiatives
Strong expertise in AI upskilling, digital capability-building, or technology-driven learning; direct experience delivering AI upskilling programs is highly valued
Proven ability to translate complex and emerging technologies into practical, applied learning experiences that drive real behavior and performance change
Track record of designing and delivering reskilling or workforce transition initiatives tied to business needs
Demonstrated success leading large-scale initiatives without direct reports, influencing senior stakeholders and peers across functions
Highly strategic thinker with a hands-on, execution-oriented mindset—able to move seamlessly from vision to delivery
Exceptional stakeholder influence and communication skills, with the ability to engage senior leaders as a credible advisor
Experience operating in complex, global, matrixed organizations

Responsibilities

Enterprise AI Upskilling Strategy & Curriculum Ownership
Own and deliver Mastercard’s enterprise AI upskilling strategy, ensuring alignment with business priorities, technology roadmaps, and workforce needs
Design and oversee a cohesive, tiered AI learning curriculum—from foundational AI literacy to advanced, role-specific and applied AI capabilities
Ensure AI learning experiences are persona- and role-based, accelerating time-to-proficiency and on-the-job application
Continuously evolve the AI curriculum to reflect emerging technologies, tools, and use cases, balancing speed, relevance, and scalability
Reskilling & Workforce Redeployment Enablement
Lead the design and implementation of reskilling pathways that support role evolution, redeployment, and future-critical capability building
Partner with Global Skilling, Talent Partners, HR Partners and business leaders to identify priority reskilling populations and skill adjacencies
Translate skills data and workforce insights into practical reskilling journeys that enable mobility and redeployment across the enterprise
Ensure reskilling initiatives are tightly linked to real roles, work, and outcomes, not abstract skill development
Business Partnership & Applied Impact
Serve as a trusted thought partner to business, technology, and HR leaders on AI capability-building and workforce transformation
Anchor all AI upskilling and reskilling initiatives to clear business outcomes, such as revenue, productivity lift, speed to proficiency, role readiness, and adoption of AI-enabled ways of working
Act as a connector across the organization to ensure end-to-end execution and adoption
Execution Excellence & Portfolio Leadership
Lead the end-to-end execution of AI upskilling and reskilling initiatives—from needs identification and experience design through delivery, adoption, and continuous improvement
Manage a complex portfolio with disciplined prioritization, ensuring focus on the highest-impact initiatives
Oversee vendor and partner relationships related to AI learning and reskilling solutions, with a strong focus on quality, scalability, and ROI
Measurement, Insights & Continuous Evolution
Define and track success metrics that demonstrate the impact of AI upskilling and reskilling on business and workforce outcomes
Partner with Global Skilling, Talent Management, and People Analytics teams to strengthen skills measurement, insights, and decision-making
Use data, feedback, and external trends to continuously refine strategy and improve effectiveness
Leadership & Culture
Mobilize cross-functional stakeholders, peers, and partners to deliver enterprise AI upskilling and reskilling outcomes
Model a culture of experimentation, continuous learning, and bias-to-action, aligned with the Mastercard Way

Benefits

insurance (including medical, prescription drug, dental, vision, disability, life insurance)
flexible spending account and health savings account
paid leaves (including 16 weeks of new parent leave and up to 20 days of bereavement leave)
80 hours of Paid Sick and Safe Time, 25 days of vacation time and 5 personal days, pro-rated based on date of hire
10 annual paid U.S. observed holidays
401k with a best-in-class company match
deferred compensation for eligible roles
fitness reimbursement or on-site fitness facilities
eligibility for tuition reimbursement

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