Senior Director, Enterprise AI Strategy, Technology Training & Transformation

UnitedHealth Group•Boston, MA

9h•Remote

About The Position

Optum Tech is a global leader in health care innovation. Our teams develop cutting-edge solutions that help people live healthier lives and help make the health system work better for everyone. From advanced data analytics and AI to cybersecurity, we use innovative approaches to solve some of health care’s most complex challenges. Your contributions here have the potential to change lives. Ready to build the next breakthrough? Join us to start Caring. Connecting. Growing together. You’ll enjoy the flexibility to work remotely from anywhere within the U.S. as you take on some tough challenges. For all hires in the Minneapolis or Washington, D.C. area, you will be required to work in the office a minimum of four days per week. Primary Responsibilities: Enterprise Workforce & Capability Strategy Define and drive a multi-year workforce capability strategy aligned to Optum Technology’s strategic priorities, including AI enablement, modernization, and evolving product/platform models Establish a clear enterprise view of current and future skill needs across lines of business Partner with CIOs and technology leaders to identify capability gaps and prioritize strategic upskilling and reskilling initiatives Align workforce capability strategy to capital planning cycles and transformation roadmaps Enterprise Learning & Enablement Frameworks Design a scalable framework for technology capability development across Optum Technology, ensuring consistency while allowing for LOB-specific flexibility Oversee prioritization and alignment of technical training, leadership development, and emerging capability programs Partner with HR and Learning organizations to ensure curriculum, vendor selection, and program delivery align to enterprise technology needs Establish governance mechanisms to track adoption, impact, and measurable capability uplift AI & Emerging Capability Readiness Lead enterprise-wide AI readiness strategy from a workforce perspective, ensuring leaders and practitioners have appropriate levels of AI literacy, technical fluency, and applied capability Develop structured pathways for emerging roles and skill domains required for future-state operating models Translate enterprise AI and technology strategy into workforce implications and capability action plans Workforce Planning & Investment Alignment Partner with Finance and HR to integrate workforce capability planning into annual and multi-year financial cycles Provide enterprise-level insight into workforce capacity trends, skill distribution, and transformation readiness Support leadership in making informed decisions regarding build vs. buy vs. partner talent strategies Executive Engagement & Change Leadership Provide senior leadership with clear, data-informed perspectives on workforce capability risks, gaps, and opportunities Develop executive-ready materials for enterprise forums, workforce reviews, and strategic planning sessions Drive change management strategies that support adoption of new skills, operating models, and leadership expectations Operate with high emotional intelligence and executive presence in navigating cross-LOB dynamics and sensitive workforce topics Operating Model & Impact This leader will: Operate as the enterprise orchestrator of workforce capability strategy across Optum Technology Partner closely with CIOs, People Business leadership, Finance, and transformation leaders to ensure alignment between workforce investments and enterprise priorities Influence without formal authority, driving adoption through structured governance, transparency, and executive engagement Build a small, high-impact team responsible for workforce analytics, planning coordination, and capability program alignment Success in this role will be defined by: Clear enterprise visibility into workforce capability gaps and future skill requirements Improved alignment between strategic technology priorities and workforce investment decisions Measurable uplift in critical capabilities, including AI readiness and engineering excellence Increased agility in adapting workforce strategy to evolving enterprise needs A durable enterprise workforce strategy framework embedded into annual planning and operating cadences You’ll be rewarded and recognized for your performance in an environment that will challenge you and give you clear direction on what it takes to succeed in your role as well as provide development for other roles you may be interested in.

Requirements

Bachelor’s degree or equivalent experience
8+ years of experience in technology strategy, workforce transformation, organizational development, or enterprise capability leadership
Demonstrated experience designing and implementing workforce or capability strategies in complex, matrixed environments
Demonstrated solid executive presence with experience advising senior technology and business leaders
Deep understanding of technology skill domains and evolving industry capability trends
Proven ability to operate through influence and cross-functional partnersh
Proven solid analytical and strategic thinking skills with the ability to translate business strategy into workforce implications
Proven exceptional written and verbal communication skills
Ability to manage sensitive workforce topics with discretion and sound judgment
Experience with AI/ML-enabled technology environments and digital transformation initiatives

Nice To Haves

Experience within complex, multi-segment enterprises
Demonstrated familiarity with enterprise workforce analytics and planning tools
Experience partnering closely with People Business and Finance in large-scale workforce initiatives

Responsibilities

Define and drive a multi-year workforce capability strategy aligned to Optum Technology’s strategic priorities, including AI enablement, modernization, and evolving product/platform models
Establish a clear enterprise view of current and future skill needs across lines of business
Partner with CIOs and technology leaders to identify capability gaps and prioritize strategic upskilling and reskilling initiatives
Align workforce capability strategy to capital planning cycles and transformation roadmaps
Design a scalable framework for technology capability development across Optum Technology, ensuring consistency while allowing for LOB-specific flexibility
Oversee prioritization and alignment of technical training, leadership development, and emerging capability programs
Partner with HR and Learning organizations to ensure curriculum, vendor selection, and program delivery align to enterprise technology needs
Establish governance mechanisms to track adoption, impact, and measurable capability uplift
Lead enterprise-wide AI readiness strategy from a workforce perspective, ensuring leaders and practitioners have appropriate levels of AI literacy, technical fluency, and applied capability
Develop structured pathways for emerging roles and skill domains required for future-state operating models
Translate enterprise AI and technology strategy into workforce implications and capability action plans
Partner with Finance and HR to integrate workforce capability planning into annual and multi-year financial cycles
Provide enterprise-level insight into workforce capacity trends, skill distribution, and transformation readiness
Support leadership in making informed decisions regarding build vs. buy vs. partner talent strategies
Provide senior leadership with clear, data-informed perspectives on workforce capability risks, gaps, and opportunities
Develop executive-ready materials for enterprise forums, workforce reviews, and strategic planning sessions
Drive change management strategies that support adoption of new skills, operating models, and leadership expectations
Operate with high emotional intelligence and executive presence in navigating cross-LOB dynamics and sensitive workforce topics
Operate as the enterprise orchestrator of workforce capability strategy across Optum Technology
Partner closely with CIOs, People Business leadership, Finance, and transformation leaders to ensure alignment between workforce investments and enterprise priorities
Influence without formal authority, driving adoption through structured governance, transparency, and executive engagement
Build a small, high-impact team responsible for workforce analytics, planning coordination, and capability program alignment