Cherilynn Castleman is a woman on a mission. With over three decades of experience as a Fortune 500 Global Sales Executive, she is now an executive sales coach and the Managing Partner at CGI LLC.
As the founder and CEO of CGI, Castleman is on a mission to help a million Women of Color in Sales achieve their dreams by 2030. This spring, she is hosting a series of live events called “Step Into the C-Suite” across five US cities to teach women the skills they need to get promoted to executive positions in their organizations or create an executive strategy for their own businesses.
“Many Black and Brown women lack financial fluency, deep connections, and ‘insider’ promotion tips to get to the top. I coach them to be too good to be ignored, and that’s what this workshop is all about,” Castleman said.
Despite her busy schedule, Castleman took the time to answer some common questions she receives, providing valuable insights into her experiences and perspectives.
Q: Why selling?
A: When I was very young, around 5 or 6, I started selling girl scout cookies and I immediately fell in love with it. There was something so thrilling about making a sale and fulfilling a need that made people happy. Looking back, I would say that was the beginning of my journey in sales.
Q: Growing up, did anyone teach you how to sell?
A: My father owned Castleman Construction, and as a child, I watched him closely as he built strong relationships with his clients. He was always willing to go above and beyond to bring their visions to life, and his dedication left a lasting impression on me. Watching him, I learned about the importance of client management, relationship building, and, at the core of it all, selling. While my father didn’t necessarily sit me down and teach me the ins and outs of selling, his approach and philosophy definitely influenced my own sales career.
Q: How long have you been in sales?
A: I’ve been in sales for over three decades as a Fortune 500 Global Sales Executive. My sales career didn’t follow a very linear route, though. In the ’80s, I studied Psychology and began my career as a social worker. I wanted to help reunite families and terminate parental rights where necessary. To secure program funding, I realized I needed to build sales skills and landed my first job selling debit insurance.
As I advanced in the industry, I encountered bigger problems. Women of Color in Sales came to me with stories of discrimination, such as being told they were “being paid enough for a woman.” These experiences fueled my drive to help women succeed, and that’s why I have the goals I do today. But, let’s not make me sound old!
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Q: Why are you specifically focused on Women of Color in Sales?
A: My focus on Women of Color in Sales is driven by the need to address the current bleak outlook for Black and Brown women in corporate America. Despite their immense potential, only a few Black women have made it to the top of the Fortune 500 list, with Ursula Burns being the only one to date. This is not enough, and we need to see more Black and Brown women breaking through the glass ceiling. Unfortunately, African American women lack the resources and tools necessary to succeed in the corporate world, as evidenced by Fortune’s article on “The Black Ceiling.” I believe that the key to success lies with the people closest to the product and the money, and Women of Color in Sales need a gateway to these people and products to make a name for themselves. I personally understand the feeling of invisibility in sales, having never been in a room with another Black female salesperson. It’s time to rewrite the narrative for Black and Brown Women in Corporate America, and I’m excited to be at the forefront of this mission.
Q: What is your #1 goal and priority moving forward?
A: My ultimate goal is to see a million Women of Color in Sales achieve their dreams by 2030, and I want to help make that happen. Black Women make up 70% of the workforce, yet there are not enough seats for us at the table. I want to train and empower women who are too good to be ignored and equip them with the confidence, motivation, financial fluency, and belief that they deserve to not just have a seat at the table, but to own the table if they want. My own daughters are great examples of what hard work and a tough attitude can achieve. If I could go from being invisible to being too good to ignore, I believe any woman can.