Cherri Bailey

Background

About Cherri Bailey

I’m a people-first leader with over eight years of experience developing and coaching high-performing teams in sales and customer experience. My passion is truly helping people grow by building training programs, coaching frameworks, and learning experiences that drive measurable results and lasting confidence. At CarMax, I led remote sales teams and created scalable onboarding and development programs that improved conversion, engagement, and overall team performance. Partnering across Marketing, Product, and Operations, I built playbooks and processes that connected strategy to execution and elevated the associate and customer experience. I’m now focused on bringing that same energy and expertise into Learning & Development and Talent Growth. I'm all about creating environments where people feel supported, challenged, and equipped to do their best work. I believe that when learning is intentional and people feel valued, performance naturally follows. Core strengths: • Leadership & Coaching • Learning & Development Program Design • Talent Growth & Engagement • Process Improvement • Data-Driven Coaching & Analytics (Salesforce) • Cross-Functional Collaboration • Employee & Customer Experience Strategy