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, adopted, 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.
Primary Responsibilities:Training Operations & Program Execution:- 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
Training Deployment, Adoption & Reinforcement:- 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
Communication, Narrative & Engagement:- 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
AI-Enabled Execution & Continuous Improvement:- 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
Stakeholder Coordination:- 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
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.
Required Qualifications:- 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
Preferred Qualifications:- 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)
*All employees working remotely will be required to adhere to UnitedHealth Group's Telecommuter Policy.
Pay is based on several factors including but not limited to local labor markets, education, work experience, certifications, etc. In addition to your salary, we offer benefits such as, a comprehensive benefits package, incentive and recognition programs, equity stock purchase and 401k contribution (all benefits are subject to eligibility requirements). No matter where or when you begin a career with us, you'll find a far-reaching choice of benefits and incentives. The salary for this role will range from $134,600 to $230,800 annually based on full-time employment. We comply with all minimum wage laws as applicable.
Application Deadline: This will be posted for a minimum of 2 business days or until a sufficient candidate pool has been collected. Job posting may come down early due to volume of applicants.
