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The Relationship Sales Expert

For more than twenty years, Cherilynn Castleman has been helping Fortune 500 clients as a global sales executive. Cherilynn has experience as both an individual contributor and a manager of enterprise sales and account teams overseeing C-level sales for complex healthcare and life sciences SaaS solutions, drawing on her decades of experience as a sales executive, executive coach, and entrepreneur. She prides herself on changing mindsets as well as instructing and inspiring others to action. 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, T-Mobile, Pinterest, Justworks, Salesforce, and LinkedIn – with extensive experience in major global markets within diverse industries.

Global Sales Executive Cherilynn is the founder and executive coach of CGI and the chief learning officer for Sistas in Sales. With over twenty years of experience in enterprise sales, she  knows firsthand what it takes to succeed as a sales professional. As an experienced entrepreneur, she knows the dedication, passion, and grit necessary to make dreams a reality. As a wife and mother, she knows the challenges of balancing family and a career and the stress of trying to do it all. With her natural talent for teaching and a drive to sell, Cherilynn uses her skills to help clients achieve sales mastery.

Writer Cherilynn contributed to a national-award-winning journalism series in the Atlanta Journal and Constitution and wrote weekly columns in local print media. She has published numerous articles on client success, entrepreneurship, sales strategies, leadership, and financial fluency. Her mission is simple: amplify readers and audiences using strength-based techniques and the power of a growth mindset.

Speaker Cherilynn’s presentation style is fast-paced, light-hearted, and fun, so come prepared for an adventure in learning and laughter. She appeared monthly on a She Means Business segment for a local NBC television affiliate and hosted weekly drive-time radio segments. Audiences will develop new skills and hone processes that are key to mastering sales. Audiences will learn about building client relationships and finding solutions with simple formats, frameworks, and tools of the trade that they can integrate into their own personal style. No matter what is going on in the world, there are important lessons that listeners can apply to their own sales careers right now.

Another Cherilynn keynote experience filled with learning and laughter

Sizzle Reel 2020… What If?

Learn from The Relationship Sales Expert

“In just a one hour session, Cherilynn shared years of hard-earned sales knowledge with our audience. Her talk was engaging, entertaining, and filled with practical, actionable advice. Everyone at the session, including some attendees with years of experience, left with new tips, frameworks, and newfound commitment to growth and taking action.”

– Jake Ritzheimer,  University City Science Center

Speaking Topics


  • Exponential Sales Growth For Post-Pandemic Success
  • How to Break the Silence and Share Your Executive Voice During These Times
  • The C Factor for Sales Success and Effective Leadership
  • Becoming An Empathic Seller Using Financial Insights & Versatility

Available For

  • Keynotes
  • Sales Kick-Offs
  • Breakout Sessions
  • Workshops
  • Podcasts
  • TV/Radio Shows
  • Seminars

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To book Cherilynn for your next event, contact us with your event details and speaker budget. 

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