Meet Cherilynn Castleman
The Woman Helping 1 Million Women Rise to Leadership by 2030
AI Sales Strategist | Global Sales Exec | Trainer/Coach
About Cherilynn
Cherilynn Castleman is a global sales coach, dynamic speaker, and passionate advocate for women in leadership. With over 25 years of experience helping professionals and Fortune 500 companies drive results, she brings unmatched energy, empathy, and expertise to every room she enters.
Through coaching, training, and keynotes, Cherilynn equips women to lead with confidence, close with purpose, and rise into decision-making roles. Her mission is clear: help 1 million women step boldly into leadership and transform the future of business.
When she’s not teaching or speaking, Cherilynn is building community, mentoring rising leaders, and showing the world what’s possible when women own their voice—and their value.
Achievements
Cherilynn Castleman has spent over two decades breaking barriers and building leaders. Her coaching and training programs have impacted global organizations, elevated hundreds of women into leadership roles, and shortened sales cycles across industries.
Linkedin sales [in]sider
2022 - 2025
SalesForce Top sales
influencer
2022 - 2025
1 million women by 2030
When I first began coaching, I didn’t expect to double the amount of outbound meetings I book each month. And I hadn’t considered that I could find joy in connecting with prospects on LinkedIn, As I transitioned into my new role as a SDR, she helped to shift my thinking. I’ve been in role for a few months and have consistently reached my quota. Cherilynn helped me achieve this.
Janine Simon
Customer Success Manager, TripActions
A good executive coach doesn’t just sharpen your skills, she sharpens your vision…
I’ve had the privilege of learning from Cherilynn for years, and what sets her apart is her unmatched ability to blend data with heart. Her guidance on building genuine rapport, leaning into collaboration, and growing your influence with integrity has shaped how I lead today.
Dr. Keisha King
Head of US Strategy, T-Mobile
Cherilynn has been my north star in this amazing and challenging 2021. She has shown me how to unlock the gifts I already encompass and blend them with new ways of being, uncovering my authentic self. Showing up authentic and trusting myself fully has truly changed my life both personally and professionally.
Sheri Olsen
Technology Sales Leader and Client Partner at T-Mobile
Cherilynn Castleman is a coach, speaker, and advocate for women breaking barriers in business. Stay connected for bold insights, resources, and opportunities to lead with impact.
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