An Exclusive Interview With Executive Coach Cherilynn Castleman

The epitome of energy, ideas, an inspiring journey, and a woman who is crystal clear about her vision and mission. Some women have an aura to them, some strange energy that can attract you with just one talk. This interview with Cherilynn has exactly been the same.  She is a classic example of when a woman decides to grow, she takes women around her to the path to success. This amazing Executive coach has been on the journey of placing women in the C-suite and helping them live their dream life.

She is a Keynote speaker, author, Executive Coach, Sales Coach, SalesForce Influencer 2022, LinkedIn Sales [In]sider 2022and a Powerful Brand Herself. 

Let’s read about her incredible journey with the Power Brand Cherilynn Castleman.

  1. Please give us a sneak peek into your business and how it all started.

I’ve been in sales for a long time since before girl scout cookies for 50 cents a box and have an experience over 30 years as a fortune 500 global sales executive. I know what it like feels like to be the only one in the room and am aware of the challenges faced by black and brown women to sit at the table of their dreams. I started coaching and training women in order to see a million of women of color by 2030, to be at the C-suite top of the leader board or build their own entrepreneurial table. Majority of the women today lack access and financial fluency to get there. That is why I coach and train black and brown women to be too good to be ignored. 

  1. What inspired you to impact women of color every single day in your line of work?

What inspired me for the transition was the fact that we have only one black woman in 65 years to work as a CEO of a Fortune 500 company. She was none other than Ursula Burns, CEO of Xerox. When Ursula was once asked about the reason behind not many women of color in the C-suite, she went on to say marketing and arts won’t help you get there. Women have to learn to be close to money and product which is nothing but sales. We have to learn how to sell. If you’re building a practice or building your own business, you have to learn how to sell. You have to learn how to deliver value. So I started coaching and training women on the nuance of financial fluency and the art of selling into the C-suite and help women understand how an executive mindset works and decide whether they want to be in that C-suite or want to sell into the C-suite.

  1. What do your coaching programs exactly have to offer other than products and sales?

I offer three things through my coaching programs:

a) I coach black and brown women to become sales entrepreneurs and offer them one-on-one coaching practice. I spend about a third of my time helping large companies recruit, retain, and elevate black and brown women. I talk with their leadership team and, and share ideas on how to see these women, basically helping them with research and studies. And I can send any of these women to you.

b) I then provide coaching and training to these women. I have a cohort where companies will give me anywhere from six to twenty women that I train for three to six months. During this duration, they learn everything from financial fluency, selling into C-suite, empathetic listening, and value-based selling. They also do group coaching so that they can learn how to deal with microaggressions, bullying, and prejudice and also build their hard skills, social selling, pandemic sales strategies, and building high-performance team 

c) Finally, the third thing I offer them through my coaching is keynote speaking which I usually do at conferences

  1. What demographic are you targeting/ What is your target audience?

The majority of my target audience is women between the age of 25 and 45. But I talk to anybody who wants and will help me accomplish my mission to hit a million women by 2030. I have had college kids contact me in the past and I’ve done interviews and events for college students, organizations, and women in sales in college, I have also coached women who are late in their careers and are moving to become chief revenue officers, and are in their fifties or sixties. When you are the only one in the room, it doesn’t matter how old you are. 

  1. How did it all start in the beginning of your coaching career when you were nowhere?

Although I’d been coaching for years, I really didn’t have a framework for it. I didn’t know if I was any good. So, I went back to school and took up an ICF-certified training program. When I came out of that program, I could coach anybody who would listen to me. Post that I started doing what I call an energy exchange. Whenever anything that somebody had, I would do an energy exchange. If they didn’t have an energy exchange, I would ask them to write, follow me on LinkedIn and support me on LinkedIn.

I coached my yoga instructor and she did yoga videos for me. I coached a web person and they designed some web pages for me.

I coached a writer and they helped edit my blogs.

I just coached people and asked them if they would do a testimonial for me. When people would end that, then they would want to start paying.

And I was constantly asking people what worked and what didn’t go well. I was committed to getting better. And my clients started having successes and pushed me to start posting on LinkedIn. I always ask my clients two things when I’m coaching. First, what was the most helpful thing they found from start to end, and second if they would like me to do something different in coaching. 

I then learned how to do a conversion coaching session. I mastered my conversion story. Now when I do a conversion story, I know that I’m converting probably 90% of the people I talk to as clients.

I started my prices so low that nobody could deny them. And then once you start, you start raising your prices until you get a no.

  1. What strategy do you think one should follow for posting content on social media?

Initially, I used to write blog posts and how-to guides but the engagement factor was low then. And then one day somebody suggested me to just write from my heart. So, following that advice I wrote a post from my heart. I was very nervous. I was very afraid and it got over 20,000 views and clicks and engagement that I could not believe. So now every Tuesday I write a post from my heart.

And so now every Tuesday I share a story, and it increases my followers. It makes people connect with me. I write about my granddaughter. I write about being a single mom and much more fun content to which people can relate.

I also do a LinkedIn live or a free webinar every other week. I have always believed in sharing my knowledge as much as I can. The more you share your knowledge, the more you create value. So just coach and consult and just give it away until you’ve mastered it and perfected it and then start charging and keep raising your prices until you get recommendations. But what matters in the whole process is that you stay true to yourself, have a mission, have a vision, and have a value story.

  1. How can people find you or search for you?

You may go to LinkedIn and look for a sales coach, a saleswoman, or a sales coach for women and you might find me there.

You can also reach out to me through my website: 


Brunda Sunil

Brunda Sunil

Founder & SEO Content Strategist

She loves all things words. Having worked as an SEO content writer for seven years in different industries. She now passionately works as an SEO content strategist and entrepreneur. She helps start-ups, solopreneurs and personal brands with high-quality SEO content for generating organic traffic through content strategy and a holistic SEO approach to rank the client’s website on google’s first page.

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