Overnight Engineering Leadership Development Program Jobs in Chicago, IL

The Senior Leadership Development Specialist program manages, facilitates, and continuously improves enterprise frontline leadership development programs that strengthen leader capability and support business priorities. This role leads end-to-end program execution, delivers engaging virtual and in-person learning experiences, and partners across regions to provide consistent, train‑the‑trainer experiences. The position works closely with the broader Talent Development team, business leaders, HR partners, regional stakeholders, internal experts, and external vendors to deliver scalable programs with measurable outcomes.

• Manage end-to-end delivery of frontline leadership development programs, including program plans, timelines, communications, participant experience, logistics, technology, vendor coordination, risks, etc.
• Coordinate regional train-the-trainer sessions for facilitators and program leads while maintaining consistent standards and adapting to local needs.
• Create clear governance, operating rhythms, stakeholder updates, and escalation paths that keep programs on track and support timely decisions.
• Partner with internal teams and external vendors to ensure deliverables meet agreed scope, quality, timing, and learner experience expectations.
• Facilitate engaging virtual and in‑person workshops, discussions, debriefs, assessments, and practice activities for leaders at multiple levels.
• Create an inclusive learning environment that encourages reflection, participation, peer learning, and application to real business challenges.
• Adjust facilitation approach based on audience needs, cultural context, group dynamics, and delivery format rather than relying solely on scripted content.
• Support facilitator readiness through train‑the‑trainer sessions, guides, observation, and feedback.
• Build trusted relationships with business leaders, HR partners, program sponsors, regional stakeholders, subject matter experts, and vendors.
• Gather business and regional needs, identify cultural considerations, and translate insights into practical program and delivery recommendations.
• Balance enterprise consistency with regional relevance to support scalable leadership development across a global organization.
• Communicate clearly with diverse stakeholders, influence without direct authority, and resolve issues with sound judgment and a collaborative approach.
• Have experience with end-to-end leadership development program management: Track participation, completion, learner feedback, behavior change, stakeholder satisfaction, and other agreed program outcomes.
• Use data and stakeholder input to improve content, delivery, operations, scalability, and overall learner experience.
• Stay current on leadership development practices, facilitation methods, learning technology, and AI‑enabled tools, and apply relevant ideas to improve programs.

• Bachelor's degree in leadership development, organizational development, human resources, business, education, or a related field, or equivalent practical experience and 5+ years of experience in leadership development, learning and development, talent development, organizational development, or a related field OR
• 9+ years of experience in leadership development, learning and development, talent development, organizational development, or a related field
• 3+ years of experience managing complex learning or leadership programs with multiple workstreams and stakeholders.
• Demonstrated success facilitating virtual and in‑person learning for leaders.
• Experience working across functions, regions, cultures, and time zones in a matrixed organization.
• Strong written and verbal communication, presentation, relationship‑building, organization, and problem‑solving skills.
• Ability to use program data and feedback to identify improvements and communicate impact.
• Experience working in a skills‑based organization, driving learning architecture to support high priority skills at all levels
• Experience using a consultative approach with diverse stakeholders
• 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

• Industry facilitation/assessment/coaching certifications (DDI, Franklin Covey, CCL, Vital Smarts, CliftonStrengths, 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/
Salary ranges may be subject to geographic differentials

We’re looking for people who bring curiosity, a learner’s mindset, and a willingness to engage with ever‑evolving technology and tools. We value adopting AI as a partner, openness to experimentation, and a shared interest in learning together on AI. Our goal is to create a culture where AI enhances—not replaces—human creativity and decision‑making. You don’t need to be an expert today; what matters is your readiness to explore, adapt, and grow with us as we integrate AI responsibly and effectively into our work.

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.

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 full‑stack, full‑lifecycle 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.