Learning Development Program Manager Jobs in Oswego, IL

Lead AI Learning Manager

The Lead AI Learning Manager is responsible for leading the strategy, execution, and ongoing operations of enterprise AI and technical education at scale. This role blends product management, program leadership, and learning expertise to build measurable, high-impact learning experiences that accelerate AI adoption, productivity, and responsible use.

Operating with the rigor of a product organization, this role owns learning roadmaps, delivery rhythms, stakeholder alignment, and outcomes. A successful candidate is expected to independently lead complex, cross-functional initiatives, translate strategy into execution, and influence senior stakeholders without formal authority. The role balances strategic thinking with hands-on delivery and team leadership.

This role is ideal for someone who is energized by continuous change, passionate about emerging technology, and excited to help shape the future of learning in an AI-enabled enterprise.

Key Responsibilities

AI Learning Strategy & Portfolio Ownership- set direction, prioritization, and long-term value of AI learning as a product.

• Execute the AI learning strategy and program plan aligned to enterprise AI priorities and workforce needs
• Operate AI learning as a product portfolio, including vision, roadmaps, backlogs, prioritization, and lifecycle management
• Define and track success metrics such as literacy, engagement, adoption, and applied impact
• Establish learning pathways that support associates throughout their AI capability journey, from foundational literacy through advanced application

AI-Native Learning Design & Innovation- Redefine how learning is designed, delivered, and experienced in the age of AI.

• Design and scale AI-native learning experiences that leverage personalization, coaching, simulation, practice, and emerging technologies to accelerate skill development
• Explore and implement innovative approaches that make learning more adaptive, contextual, and embedded within the flow of work.
• Identify opportunities to apply AI across content development, learning operations, learner support, measurement, and program administration
• Evaluate emerging learning technologies and AI capabilities to improve learner experience and organizational outcomes

Cross-Functional Alignment & Enterprise Partnerships- Influence, coordinate, and integrate across a matrixed organization.

• Navigate and influence across matrixed org of Technology, Corporate, and Frontline learning to deliver a cohesive AI education plan grounded in needs analysis, personas, and learning experiences
• Partner with Functional, HR, Change Management, and Business leaders to ensure learning is practical, applied, and aligned to real tools and workflows
• Partner with the broader Enterprise AI Enablement organization to translate tools, responsible usage, and domain needs into learning programs

Program Delivery, Planning & Continuous Improvement- Bring executional rigor and operational excellence.

• Lead quarterly planning, delivery rhythms, retrospectives, and continuous improvement for AI learning initiatives
• Communicate progress, insights, and outcomes clearly to senior stakeholders
• Develop scalable governance and operating models that ensure quality, consistency, and responsiveness to change

Platform, Vendor & Content Management- Consider scale, quality, and ecosystem management.

• Own vendor relationships, learning platforms, and content strategy to ensure scale and quality
• Integrate platform, content and broader vendor decisions into the enterprise AI platform strategy, balancing need to accommodate rapid change and foundational durable concepts.
• Partner with AI Enablement leadership on optimal use of budget across platform and content providers.

Required Qualifications

• 7+ years of experience in program management, product management, learning & development, or technical enablement.
• Demonstrated experience leading complex, cross-functional initiatives in ambiguous environments.
• Strong understanding of modern product and agile practices. Excellent stakeholder management, communication, and influencing skills.
• Demonstrated curiosity, experimentation mindset, and passion for emerging technologies
• Ability to translate complex technical innovations into practical, business-relevant capability-building strategies

Preferred Qualifications

• Experience building or scaling enterprise AI, data, digital, or technical learning programs
• Experience leading workforce transformation initiatives enabled by AI or emerging technologies
• Experience applying AI tools to redesign workflows, learning experiences, or operational processes
• Familiarity with skills-based talent and learning models
• Experience with learning platforms, learning analytics, and capability measurement frameworks