About Cherilynn

Cherilynn Castleman, MBA, Head of Education & Growth

Cherilynn Castleman is the Managing Partner and Executive Coach at CGI, a consulting and training firm specializing in sales training, leadership development and executive coaching. As a sales coach and internationally renowned sales expert, Cherilynn teaches clients how to develop highly effective growth strategies and innovative go-to-market models to increase sales productivity and drive revenue. For over 20 years, Cherilynn has been helping forward-thinking sales professionals and small business leaders solve their toughest sales, leadership, and culture challenges. Her trainings and insights equip her clients with the skills and knowledge they need to master executive sales, unlock potential, and maximize performance.

Cherilynn started her career in social work, but soon discovered she needed to develop sales skills to secure funding for her program. To hone her sales skills, Cherilynn landed a job selling life insurance door-to-door and quickly realized her talent for selling. Her success as a sales leader created opportunities for advancement, growing her career to sales manager, vice president, and ultimately general manager. As a general manager, Cherilynn carried profit-and-loss responsibilities and closed deals worth tens of millions of dollars in Asia, Central and South America, Europe, and the United States.

With over 20 years of enterprise C-level selling and relationship development experience with complex Healthcare and Life Sciences SaaS solutions, Cherilynn has experience as both an individual contributor and manager of enterprise sales and account teams. Her clients and experiences include: United Healthcare, Anthem, the Blue Cross Blue Shield Association (thirty-eight independent BCBS companies), Merck, Wyeth, Johnson & Johnson, Roche, Eli Lilly, Pinterest, iOpening Enterprises, Justworks, and LinkedIn.

Drawing on her decades of experience as a general manager, educator, executive coach, and entrepreneur, Cherilynn founded CGI in 2018. In her coaching and training practice, Cherilynn prides herself on changing mindsets as well as instructing and inspiring others to action. Her goal is to ensure her clients are too talented to ignore.

Cherilynn lives in Washington, D.C. with her husband and enjoys cycling, practicing yoga, and spending time with her two adult daughters and their families.

Cherilynn Castleman brings her 20+ years of experience as a sales executive to the table in her work as a sales trainer, consultant, and executive coach. With a natural talent for teaching and a drive to sell, Cherilynn uses her skills to coach and train other sales professionals. Clients and experiences include: United Healthcare, Anthem, Johnson & Johnson, Pinterest, Justworks, and LinkedIn.


Happy Clients

We’re happy to furnish references upon request.

Join Our Email List