Director, Technology Training Operations & Workforce Enablement

Primary 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
• Cook up day-to-day execution, aligning, sequencing, and delivering technology training efforts across lines of business
• 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

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
• Ability to leverage 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)