From Episode 03 – September 2026
Be known for what you know.
Make your expertise visible. Give the right people a reason to connect.
Cherilynn brings together decades of sales experience and daily AI practice to help women reach the table of their dreams. Her approach to LinkedIn starts with knowing what you stand for, showing up consistently and building relationships through the conversations that follow.
AI Asset: The LinkedIn Operating System
What you're building
Your LinkedIn OS gives your AI the context to find post angles that sound like you.
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The Guest
The founder in the room for Episode 03.
MANAGING PARTNER & EXECUTIVE SALES COACH · CGI Coaching & Training, LLC · USA
Meet Cherilynn Castleman
A former Fortune 500 sales executive, Cherilynn coaches Harvard Business School MBA students and teaches at the Harvard Division of Continuing Education. She also works with revenue teams at Salesforce, Amazon, LinkedIn and Experian, helping them navigate selling in the age of AI without losing the human relationships at the centre of great sales.
“Sales is a gateway skill, and AI is a gateway technology. If you combine AI and sales, you can open any door so that you can sit at the table of your dreams.”
Founder tech stack
What Cherilynn runs on — and keeps human
Cherilynn uses AI throughout her work, but she keeps the final judgement firmly human — especially when it comes to facts, voice and people.
Facts: I verify every number. AI invents plausible figures, and plausible is the dangerous part.
Voice: I read it aloud, standing up. If I would not say it in a meeting, it does not publish.
People: Anything a person will feel, I write. AI does not speak for me to someone who trusts me.
The wrap: AI writes the fast first draft. My judgement writes the final one.
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