Head Of Learning Development Jobs in Chicago, IL

The Senior Learning & Development Specialist is responsible for designing, building, and maintaining a future-ready skills-based learning architecture that equips coworkers and leaders at every level to grow, adapt, and perform in a rapidly transforming business environment. This role sits at the intersection of learning strategy, skills taxonomy, and capability development, ensuring that learning content, pathways, and experiences are directly aligned to critical enterprise skills, proficiency levels, and business priorities including AI transformation and business transformation.

Partnering closely with the Director of Learning Strategy & Design, the broader Talent team, HR Business Partners, and business stakeholders, this role will aid in building a scalable, globally consistent skills-based learning ecosystem. This includes translating CDW's skills taxonomy and leadership capability model into structured, multi-modality learning paths that ensure coworkers and people leaders can build the skills they need today and develop the capabilities required for tomorrow.

What you'll do
As a Sr. Learning & Development Specialist, you will shape and deliver transformative learning experiences that drive enterprise-wide skills development.
Build and maintain skills-based learning architecture aligned to enterprise skills taxonomy
Map learning experiences to identified Workday Skills Cloud and proficiency levels
Design structured multi-modality learning paths in support of high priority skills
Build and maintain skills content roadmap aligned to business priorities
Develop prioritized learning pathways for critical skill gaps
Design, build, and deliver high-impact learning solutions using modern instructional design technology and principles
Apply appropriate training methods and modalities based on learning objectives and audience needs
Establish and maintain governance frameworks and SOPs for development assets
Ensure consistency and quality across all learning deliverables
Leverage learning technologies and platforms to enhance learner engagement
Design, build, and deliver high-impact learning solutions using modern instructional design technology and principles
Apply appropriate training methods and modalities based on learning objectives and audience needs
Establish and maintain governance frameworks and SOPs for development assets
Ensure consistency and quality across all learning deliverables
Leverage learning technologies and platforms to enhance learner engagement
Champion AI fluency across all learning solutions and modalities
Identify opportunities to integrate AI-enabled tools and technologies into learning design
Support enterprise transformation by ensuring learning architecture evolves at pace of business change
Stay current with emerging AI trends and their implications for learning and development
Foster a culture of innovation and adaptability within the learning organization

What we expect of you
Bachelor's degree in Human Resources, Leadership Development, Organizational Development, or related field (or equivalent experience)
5+ years of experience working in learning & development roles that have a combination of instructional design, facilitation, program management, consulting, etc.
5+ years of experience creating, activating, and evolving development solutions for both the individual contributor and people leader populations
5+ years of experience working in a skills-based organization, driving learning architecture to support high priority skills at all levels
5+ years of experience using a consultative approach with diverse stakeholders
5+ years of experience using learning technology platforms (e.g., Workday LMS) and design tools such as Articulate, Synthesia, Camtasia, Canva, Brain Shark, and other AI Enabled technology/tools/skills-based systems, etc.
Experience using project management tools (e.g., Monday.com; Smartsheet, etc.)
Strong communication skills with the ability to simplify and convey complex concepts
Proven ability to operate independently and navigate ambiguity in a fast paced environment

Preferred skills, experience, and qualities needed (optional)
Industry facilitation/assessment/coaching certifications (DDI, Franklin Covey, CCL, Vital Smarts, Clifton Strengths, DISC, Birkman, Hogan, Coaching, etc.).
Professional certifications (ATD, SHRM, or similar).
AI certifications that support learning implementation

Pay range: $84,000 - $119,000 depending on experience and skill set
Annual bonus target of 5% subject to terms and conditions of plan
Benefits overview: https://cdw.benefit-info.com/

CDW is committed to being an AI-fluent organization

Additionally, CDW is committed to fostering an equitable, transparent, and respectful hiring process for all applicants. During our application process, our goal is to understand your experience, strengths, skills, and qualifications. As an AI forward company, we see AI not just as a tool, but as a catalyst for new ways of thinking, creating, and communicating. We encourage candidates to embrace an AI mindset, one that's curious, adaptive, and ready to explore what's possible. We welcome thoughtful use of AI to expand your perspective and elevate how you share your story, while ensuring your application remains rooted in your own background, judgment, and voice.

About Us

CDW is a Fortune 500 technology solutions provider that helps businesses, government, education, and healthcare organizations achieve what's possible through technology. What makes CDW different isn't just what we do-it's how we do it. At CDW we act as one-building trust, speaking candidly, and working together to achieve more. We play to win-focusing on what matters most and delivering for our customers. And we think forward-staying curious, moving fast, and continuously learning. We believe meaningful work happens when people feel supported, heard, and empowered to contribute. That's why we think of ourselves as coworkers, not just employees-working together to solve complex challenges and deliver real impact for our customers and communities.

As a fullstack, fulllifecycle technology partner, CDW brings deep expertise, strong relationships, and broad industry knowledge to help turn ideas into outcomes. When you join CDW, you become part of a collaborative environment where your work matters, your growth is supported, and your contributions help shape what's next.

Together, we deliver the full promise of what technology can do. Together, we Make Amazing Happen.

CDW is an equal opportunity employer. All qualified applicants will receive consideration for employment without regards to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status or any other basis prohibited by state and local law.