Director of AI-Era Skilling Transformation

Microsoft is redefining how people skill in the age of AI. As the Director of AI-Era Skilling Transformation you will lead the disruption of skilling into a dynamic, AI-powered, in-flow experience that meets the evolving demands of work. This role is central to operationalizing our vision to Work to Skill via Agentic enabled Work Embedded Skilling - a new SaaS category that enables real-time, personalized, and scalable development across the enterprise.  

Why This Role Matters 

This is not just a job; it’s a movement. You will help Microsoft, and its customers close the productivity gap by enabling “always skilled” talent. Your work will shape the future of learning and skilling.  

The Director, AI-Era Skilling Transformation, is a pivotal role focused on disrupting how Microsoft’s global workforce builds and evolves future-ready skilling. This role exists to deliver transformative skilling experiences that intrinsically motivate individuals and teams to skill through exploration, demonstration, and real-world experiences. You’ll collaborate across Academies, Engineering, Human Resources, Data Analytics, and global learning partners, applying Agile methodology to provide input into strategy, define success metrics, and deliver solutions that build critical skills with measurement, confidence and clarity. 

Microsoft’s mission is to empower every person and every organization on the planet to achieve more. As employees we come together with a growth mindset, innovate to empower others, and collaborate to realize our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.

Responsibilities

• Thought Leadership:  
  • Champion the shift from episodic learning to continuous, AI-augmented skilling embedded directly into the flow of work through business aligned co creation.  Advance foresight practices ensuring anticipatory and proactive approaches to identifying, pursuing and building skills while building systems that keep content, modalities and feedback up to date and relevant to end users.   

• Portfolio Development, Management and Evolution:  
  • Develop, manage and evolve a comprehensive portfolio of agentic enabled and infused skilling experiences meeting the on-going needs of Microsoft’s organizations, teams and individuals to skill at the pace and scale of change.  Adult learning and neuroscience expertise is expected to drive high quality end user experiences, while innovating at speed to skilling revolution.   
• Innovation & Productization: 
  • Collaborate and co-create on the design and deployment of intelligent skilling agents powered by Microsoft Copilot. Define and scale new learning experiences that triple upskilling speed and halve time-to-competency. 

• Cross-Functional Collaboration:  
  • Partner with Academies Engineering, HR, Product, and Business stakeholders to integrate skilling into workflows, tools, and platforms. Ensure co-creation and business centricity with business outcomes aligned to measurable <