Director, Learning & Development - AI Upskilling & Reskilling

Our Purpose
Mastercard powers economies and empowers people in 200+ countries and territories worldwide. Together with our customers, we're helping build a sustainable economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation, partnerships and networks combine to deliver a unique set of products and services that help people, businesses and governments realize their greatest potential.
Title and Summary
Director, Learning & Development - AI Upskilling & Reskilling
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.
Key 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
Experience & Capabilities• 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
Mastercard is a merit-based, inclusive, equal opportunity employer that considers applicants without regard to gender, gender identity, sexual orientation, race, ethnicity, disabled or veteran status, or any other characteristic protected by law. We hire the most qualified candidate for the role. In the US or Canada, if you require accommodations or assistance to complete the online application process or during the recruitment process, please contact [email protected] and identify the type of accommodation or assistance you are requesting. Do not include any medical or health information in this email. The Reasonable Accommodations team will respond to your email promptly.
Corporate Security Responsibility
All activities involving access to Mastercard assets, information, and networks comes with an inherent risk to the organization and, therefore, it is expected that every person working for, or on behalf of, Mastercard is responsible for information security and must:

• Abide by Mastercard's security policies and practices;
• Ensure the confidentiality and integrity of the information being accessed;
• Report any suspected information security violation or breach, and
• Complete all periodic mandatory security trainings in accordance with Mastercard's guidelines.

In line with Mastercard's total compensation philosophy and assuming that the job will be performed in the US, the successful candidate will be offered a competitive base salary and may be eligible for an annual bonus or commissions depending on the role. The base salary offered may vary depending on multiple factors, including but not limited to location, job-related knowledge, skills, and experience. Mastercard benefits for full time (and certain part time) employees generally include: 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; and many more. Mastercard benefits for interns generally include: 56 hours of Paid Sick and Safe Time; jury duty leave; and on-site fitness facilities in some locations.
Pay Ranges
Purchase, New York: $168,000 - $269,000 USD