Director, Technology Training Operations & Workforce Enablement

UnitedHealth Group•Eden Prairie, MN

1d•$134,600 - $230,800•Hybrid

About The Position

The Director, Technology Training Operations & Workforce Enablement serves as the operational engine behind our technology training and workforce strategy. In this role, you will bridge learning strategy and operational execution, translating enterprise technology training priorities (including AI, software engineering, and modern infrastructure) into coordinated, executable programs—ensuring learning initiatives are effectively deployed, adoption, and embedded across teams. Acting as a learning operations leader, you will drive day-to-day execution, alignment, and communication of technical training efforts across lines of business. You will operate with a high degree of ownership, responsiveness, and attention to detail to operationalize learning strategy, consolidate fragmented efforts, and enable consistency and scale across technology upskilling programs. Success in this role will be defined by the effective, coordinated execution of technology training programs, increased adoption and practical application of new capabilities by teams, clear visibility into progress, and streamlined, non-duplicative training efforts across our organization. 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.

Requirements

8+ years of experience in learning and development (L&D), training operations, or workforce enablement roles
Solid expertise in program operations, learning methodologies, or training deployment, with experience working alongside technology teams
Experience driving day-to-day execution (including tracking milestones, dependencies, risks, and outcomes) in a fast-paced, matrixed environment
Solid communication and stakeholder coordination skills, with experience tailoring messaging and delivering updates to senior leadership
Experience leveraging productivity, collaboration, or AI tools to enhance operational efficiency
Ability to translate complex or technical concepts into clear, actionable, and learner-friendly messaging

Nice To Haves

Experience working within complex, multi-segment enterprises
General familiarity with technology domains (e.g., software engineering, cloud, data science, or AI/ML)
Familiarity with enterprise learning platforms (LMS), digital enablement tools, and program tracking tools
Experience supporting large-scale workforce upskilling, capability building, or transformation efforts
Professional certification in Learning & Development (e.g., CPTD) or Change Management (e.g., Prosci)

Responsibilities

Operationalize enterprise technology training strategy into clear plans, workstreams, and deliverables
Drive day-to-day program execution, including tracking milestones, dependencies, risks, and outcomes for training initiatives
Coordinate across enterprise learning organizations, CIO teams, and stakeholders to ensure technology training efforts are aligned, sequenced, and delivered effectively
Identify and resolve execution gaps, capacity constraints, and overlaps across learning initiatives
Ensure technology training programs (including AI upskilling and core technical capabilities) are effectively deployed across teams and translated into practical, day-to-day application
Reinforce learning through structured follow-ups, communications, and engagement strategies that drive adoption
Partner with technology leaders to embed training into team routines, workflows, and ways of working
Monitor adoption signals and adjust learning enablement approaches to improve engagement and impact
Translate technical training content and learning strategies into clear, accessible communications tailored to different audiences
Develop and deliver materials that help “land” complex technology concepts and training in a way that resonates with teams
Lead large enterprise learning events, workshops, and engagement efforts to reinforce capability building
Ensure consistent messaging and alignment across training-related communications
Use enterprise-approved AI and digital tools to accelerate program coordination, content adaptation, and insight generation
Apply data-assisted analysis to identify trends in training adoption, engagement, and effectiveness
Continuously refine training operations based on feedback, data, and evolving enterprise needs
Promote practical, responsible use of AI within both training content and learning execution processes
Act as a central coordination point across enterprise learning organizations, CIO organizations, HR, and enterprise stakeholders
Provide clear visibility into training progress, risks, and outcomes
Support senior leadership with concise, execution-focused updates and insights
Influence alignment across a matrixed organization without formal authority