Keynote Speaker

The Relationship Sales Expert

Cherilynn Castleman has over 30 years of experience as a Fortune 500 Global Sales Executive. Drawing from her own career success, she is passionate about the opportunities available for empowered women. She knows dedication, passion, and grit are essential when it comes to making your dreams a reality. She has helped thousands of sales individuals excel in their careers and go on to overachieve quota, set new sales milestones, and get promoted. Cherilynn’s presentation style is fast-paced, light-hearted, and fun, so come prepared for an adventure in learning and laughter.

A truly gifted storyteller, Cherilynn is highly sought-after for events both as a keynote speaker and panel moderator and receives glowing praise from event hosts.  Cherilynn speaks to the places where sales, business, and diversity intersect, moving sellers closer to their goals,  people closer to their best lives, and companies closer to their ideal identities. She has spoken at and moderated panels for LinkedIn, T-Mobile, Salesforce, Experian, Amazon, Pinterest,  Spotify, SAP, Garner, and Twilio among many others. , Her writing has been featured in LinkedIn, Sales Hacker, HubSpot, Salesforce, Entrepreneur, and Yahoo Finance.

Cherilynn regularly receives rave reviews of her speaking engagements, such as: “Cherilynn was an incredibly polished speaker, and her content was challenging, insightful and inspiring. The presentation definitely put me in a better headspace about how I can continue my growth as a person, and that it will effectively translate into my growth as a professional.” (LinkedIn Sales Executive)

The first time we ever had Cherilynn speak on a panel at Sales Hacker, the audience was electrified — and our team was, too. Every word out of her lips is fire! Inspiring, infectious, and awe-inspiring. Our team Slack channel was buzzing: Can we book Cherilynn for like 1 million more events? SERIOUSLY!!  I honestly just want a constant Cherilynn talk track happening so that I can constantly be inspired and motivated no matter the circumstance. Cherilynn’s experience and passion — her determination to be a change agent and enable others to do the same, to build a better tomorrow, and to rise the tide for all — is nothing short of extraordinary.

– KENDRA FORTMEYER, Senior Content Marketing Manager, Sales Hacker / Outreach

With her natural talent for teaching and a drive to sell, Cherilynn uses her skills to help clients achieve sales mastery. She teaches the key elements of successful sales, like deep relationships, immersing yourselves in the client’s world, financial fluency, executive presence, leveraging empathetic listening and curiosity, and understanding how to use your superpowers to create customer solutions.

Cherilynn has been recognized by: 1) Salesforce as a Tops Sales Influencer; 2) Selling Power as America’s Best Sales Speakers (2023); and 3) LinkedIn as a LinkedIn Sales [In]sider. Author of the best-selling book: What’s in the C.A.R.D.S.?: 5 Post-Pandemic Sales Strategies.

Inquire about Cherilynn’s availability and fees.

Download a complete list of topics and learning outcomes.

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

Selling into the “C-Suite”: Recession-Proof Sales Strategies

Diversity Drives Sales: Explore Tactics to Recruit, Retain and Elevate a Diverse Salesforce

Breaking the Glass Ceiling:  Frameworks insights to open doors & break barriers

Available For

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

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

Download a complete list of topics and learning outcomes.


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