Sr. Training Program Manager – 1099 Contract

Job Summary Join a passionate and growing Workforce Development team dedicated to helping organizations build skills, accelerate adoption, and achieve measurable business outcomes through learning. As a Sr. Training Program Manager, you will lead large-scale customer training programs, drive operational excellence, and serve as a trusted advisor to internal and external stakeholders. This role is ideal for a collaborative, customer-focused professional who is energized by learning and continuous improvement.

What you will do Serve as primary customer contact for enterprise and/or complex customer training programs. Develop and implement plans for global teams and schedules to fulfill contracts and subcontracts. Monitor technical, cost, and schedule performance and program utilization to ensure specified objectives are met. Develop and maintain program performance standards. Own program success; identify, assess, monitor, and mitigate risks throughout the program life cycle. Make curriculum recommendations to leadership based on customer interest, engagement, and purchasing patterns.

Monitor market conditions in the training industry and work with leadership to develop sales, marketing, and product standards for maximum market penetration and profitability. Analyze course feedback metrics to ensure quality benchmarks are met and manage corrective action when necessary. Lead key Workforce Development initiatives that impact program customers. Effectively manage multiple large training programs. Make recommendations for process improvements and automations to improve workflow efficiency and accuracy.

Track and report program progress to key internal and external stakeholders. Monitor and identify areas to achieve operational efficiency, program improvement, issue resolution and project escalations. Work closely with customer training POCs to manage customer expectations to ensure customer satisfaction and improve customer engagement. Develop and implement corrective actions for any performance metric that is not met. Take ownership of customer training outcomes to ensure customer satisfaction and success. Work with all levels of internal and external clients.

Work with Business Development Team on program success and overall communications with the customer. Report program status and risk to senior management and key stakeholders. Leverage superior written and verbal communication skills to influence customers' training decisions and maximize training consumption. What we expect of you Bachelor's degree in a related field or equivalent experience. 7+ years of experience in a customer success, engagement manager, or program management role or 5+ years of experience with a Master's degree.

Excellent use of visual, oral, and written communication skills. Pay range: $120-144/hr 1099 depending on experience and skill set CDW is committed to being an AI-fluent organization 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. 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 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.      At CDW, we make technology work so people can do great things. We are a leading multi-brand technology solutions provider to business, government, education and healthcare customers in the United States, the United Kingdom and Canada.

Our coworkers across the globe are working together to bring technology to life for our customers by solving complicated IT business challenges, providing outstanding service, and orchestrating the technology landscape to optimize our customers’ performance.