Keynote Speaker

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

Virtual Live Sales and Leadership Development Training

As the economy continues to recover from the pandemic, modern consumers expect more out of their salespeople. The key to success in this new sales environment is the ability of sales professionals and entrepreneurs to empathetically connect with their customers and use the insights gained from these connections to collaborate with clients and tailor solutions to fit their specific needs.

Financial Fluency

Move wider and higher up your client’s organizations

  • Learn while doing actual research for current clients
  • Discover how financial results drive strategy
  • Learn rapid research techniques
  • Link what you sell to what clients buy
  • Parse financial statements to find connections between client’s pain and your product
  • Employ corporate finance as a sales tool
  • Build concrete financial skills needed to sell into the C-suite and to move into or master enterprise sales
  • Develop financial fluency to find hidden and unique new business opportunities

Versatility and Social Selling™

Connect with people in a way that you have never connected before

  • Learn the simple and effective frameworks to gain the key insights you need to sell anything to anyone and manage even the most demanding clients
  • Increase versatility, the single most powerful skill you can learn in the client relationship space
  • Become more effective saleswomen and sales leaders
  • Develop better relationships with customers and team members
  • Increase levels of support and respect

Post-Pandemic Sales Strategies

For remote selling and connecting with clients

  • See what’s in the CARDS as we get ready for 2021 and beyond
  • Leverage empathy to create authentic connections, strengthen client relationships and drive sales success
  • Learn the keys to success in this new sales environment
  • Reimagine, reinvent, and recommit to focusing on connecting with clients and customers

Selling into the “C Suite”

Increase your confidence so you can have C-level conversations

  • Understand the executive mindset
  • Increase the speed and size of deals by moving up and across your client’s organization
  • Develop social relationships and share insights for sales optimization
  • Build confidence, knowledge, and skills to develop strong transformative partnerships with your clients

Building High Performance Sales Teams

Leverage the value of your team to drive performance

  • Learn three steps to discover weaknesses and strengthen them to achieve mastery
  • Ensure clarity of expectations
  • Implement evaluation of actual performance
  • Develop and maintain the motivation to sustain and meet expectations
  • Provide support within the sales team and for the individual salesperson

Empathic Listening

Develop a more attuned ear to gain insight that occurs in the space between words

  • Refine your ear and become more closely attuned to your client’s and team’s priorities and pain points
  • Discover the inner state of stillness and an outer stance of being fully present
  • Harness authentic empathy and powerful questions to better understand client’s needs
  • Develop the ability to hear what’s not being said
  • Learn techniques to dramatically accelerate your productivity

Living in Balance

Remember how amazing you truly are

  • Find work life balance and interpersonal harmony
  • Prioritize Selfcare
  • Inner work – Peace and joy from within with meditation, mindfulness, and gratitude
  • Discover and achieve what makes your heart sing
  • Overcome fear, grief, addition, regret, and pain
  • Stop self-limiting beliefs

Leveraging Your Inner Brilliance:

Step up your game as a woman & take your career to the next level

  • Discover the importance of adapting to your surroundings and being prepared to meet our next opportunity.
  • Learn how to break the silence and share your voice as a leader during these times
  • Explore mentoring, sponsoring, advocacy, and coaching
  • Develop tools to take on your growth journey to realize your full potential and become too good to be ignored.

Keynote Topics

  • Safe Conversations: Create a SAFE space to have the four critical Diversity, Equity, and Inclusion. (DE&I) conversations every executive and leader need to have during these times
  • How to Attract, Hire, and Retain a Diverse Salesforce: Today, investing in the development and retention of a gender-diverse salesforce and sales leadership team is more than just honoring a commitment to DE&I – it is a smart business decision
  • The Power of Your Ask: Getting What you want: (Getting Comfortable with “No”) Have you ever felt uncomfortable asking for something or been afraid to ask because you fear rejection? It’s hard not to take “no” personally and find the confidence to ask for what you want.
  • Get an A+ in Mentoring: Navigating your sales career in a shifting economy is easier with support from those who might have more expertise, those you trust, or those who have a unique outside perspective. The right mentor can help you aim higher, dream bigger, and achieve greater career success even as the economy is in a recovery period.

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


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