Sales Executive Wants You to See Her
Cherilynn Castleman, the product of a hardworking family who built their way to success, wants you to listen to her story. And maybe, you will see her for who she is: a strong, competent, and dedicated sales executive. She loves to sell—almost as much as she loves food, according to the self-proclaimed “dining hobbyist.”
“In sales, I believe in the rule of seven,” Cherilynn says with confidence. “You have to tell me no seven times.” She is “the relationship sales expert” and the author of the book, What’s in the C.A.R.D.S.? 5 Post-Pandemic Sales Strategies. She has a deep reservoir of knowledge, experience, and stories.
She speaks calmly yet is focused on her goal: reaching 1 million Black women in the sales sector. From her home in Sarasota, Florida, Cherilynn leads CGI, a firm that specializes in leadership development, executive coaching, and sales training. No matter what table you want to sit at, “I can help you be too good to be ignored,” Cherilynn states, as smoothly as glass.
Born in Minneapolis, the oldest of four children (two sisters and a brother), she moved to Iowa when she was five and Denver at 10. Her DNA gives her a youthful glow that belies her age—which she guards as if it was the secret to blockchain and trillions of dollars. “I think people would die if they knew how old I was!” While her peers are content to retire to the good life of days without an agenda, a clock or a boss, that’s not her modus operandi.
Why should she have to fade into the Florida sunset? Cherilynn, the divorced mother of two grown daughters and two grandchildren, is a matriarch leading by example. Her youngest daughter, Jálynn Castleman-Smith, describes her mother as “driven.” She’s determined to make a difference.
I started selling Girl Scout cookies when I was about five or six years old, and I loved it!
For the Love of Selling
“I started selling Girl Scout cookies when I was about five or six years old, and I loved it!” says Cherilynn. She would load her wagon with cookies and go “up and down the block” with her oldest brother. Back then, she was a top performer, at a time when a box of cookies sold for less than $1. Cherilynn would be affiliated with the Girl Scouts for 30 years.
Her father owned Castleman Construction, a remodeling business specializing in kitchens, bathrooms and basements. “I watched my dad establish relationships,” she says. He helped his clients create a vision; then, he would execute and deliver on that vision. “It blew people away that he could deliver the vision, and then some.” Watching her dad was her apprenticeship. “That’s how I learned about sales and client management and building relationships with clients,“ says Cherilynn, as if revealing a treasured family secret.
Her sales career had an unusual start. After attending on an academic scholarship from Occidental College in Los Angeles, California, to pursue a degree in psychology in 1980, her first job was as a social worker—she would receive an executive MBA years later in 2003 from Colorado State University. Cherilynn had a caseload of women who had been charged with failure to protect due to their boyfriends or other men in their lives murdering a child. Her goal was to unite families when possible or recommend the termination of parental rights to the court.
During her tenure, she secured funding from the United Way, but it was always a struggle. The “voracious reader” learned a valuable lesson after reading about selling. “I realized I needed to build sales skills,” she confessed.
To build her skills, she got a job selling what was then called “debit insurance,” also known as industrial or home service insurance. This insurance product was designed to help policyholders pay for the cost of funeral arrangements. The benefit was usually less than $10,000 and targeted a low-income clientele.
Policyholders paid their premiums directly to the insurance agents who came to their homes. Cherilynn says they were small burial policies. “People hung a little envelope on the door in which they put money every week or every other week, or whenever they got paid. We were known as the insurance man in the community.”
“I loved selling, and it never bothered me,” she states. She will never forget the impact that her selling had on families. “I remember young airman who drove off the road [and died] and having to take that check to his wife and toddler. That’s what insurance was about.”
Her wanderlust urged her to live abroad. In college, she lived in the international dorms. Eventually, she would move to Europe to sell insurance to ex-pats and the military. She became a top performer and was promoted to assistant general manager—she never looked back.
My struggle has always been [dealing] with sales leadership, their egos, the microaggressions, the bullying, the prejudices.
In her hit song, “I Wish I Knew How It Would Feel to Be Free,” released in 1967, Nina Simone sang, “I wish I knew how it would feel to be free. I wish I could break all the chains holding me. I wish I could say all the things that I should say.” This song is about oppression, something Cherilynn knows about firsthand.
The American workplace is transactional, where you exchange your time for money—with the hope of upward mobility. But underrepresented groups like Black women are often used, pushed aside, or worse, not even seen. Despite her success generating tens of millions of dollars in sales at several companies, including American National, American Express Financial Services, Skila, Prudential, and Advanced Health Media, she faced discrimination.
She is clear that “I never struggled with clients. My struggle has always been [dealing] with sales leadership, their egos, the microaggressions, the bullying, the prejudices. That’s what has always been my obstacle.”
“It did hurt me,” Cherilynn says in a somber voice, referring to being overlooked for opportunities. Prior to going out on her own in 2019, the last ten years had been rough. She was passed over for a promotion after closing a multimillion-dollar deal. “I led the deal. I led the request for proposal.” And she worked with her coworkers to get the job done. They all got promoted, but she didn’t. She packed up her office and walked out, with the intention of never returning. To bring her back, the CEO promoted her.
Black at Work
Nina Simone once said, “Anyone who has power only has it at the expense of someone else, and to take that power away from them, you have to use force because they’ll never give it up from choice.” In Cherilynn’s case, the “force” of economic harm was her only leverage.
The big picture for Black women is bleak. The Fortune 500 list has been published since 1955, and out of 1,800 CEOs, only 19 have been Black. Ursula Burns became the first Black women CEO of a Fortune 500 company in 2009. She led Xerox from 2009 to 2016, leaving the board of directors in 2017 after the company split into two entities: Xerox and Conduent.
In a Fortune article titled “The Black Ceiling: Why African-American Women Aren’t Making It to the Top in Corporate America,” Ursula Burns says, “Black women who do make it often end up in support positions rather than the operational roles that lead to CEO jobs. HR isn’t going to get you there. Communications and the arts aren’t going to get you there. The juice lies with people who are close to the product and the money.”
I know what it is like to feel invisible.
A light bulb went off in Cherilynn’s head. “This is why I have never been in a room with another Black female salesperson.” In a LinkedIn post, Cherilynn wrote, “I know what it is like to feel invisible.” I was one of three black women who worked on the executive floor; the others were administrative assistants.
She wrote about flying with her male peers in business class, generating millions of dollars in revenue, parking her luxury car next to theirs, socializing with them at events, dinners and leadership retreats, and riding the elevator to the top floor with them. After all those interactions, they would mistakenly call her by the names of the executive assistants.
To this day, she doesn't know what she could have done differently to be seen. That’s why she decided that she had to do something about it.
A Seat at the Table
The slights she felt from her male colleagues brought back painful memories of elementary school, where she had dreamed of eating at the “hot lunch table.” At the time, there was a hot and a cold lunch line. Her mother would send her to school with a bag lunch; she would get in line to purchase milk and sit with other kids who had carried their lunches to school. This was the “cold lunch table.”
In the hot lunch line, the ladies served kid-favorites like Sloppy Joes and French fries. Those students would sit with other kids at the hot lunch table. “I sometimes get tears in my eyes. It’s very hard for me to think about what it was like as a little girl not being able to sit at the hot lunch table.”
The slights continue today. Black women make up seven percent of the workforce. They are “severely underrepresented in leadership positions, based on information in the article “The ‘Angry Black Women’ Stereotype at Work,” published in the Harvard Business Review. They encounter stereotypes too. The authors of the article state, “When some people see a Black woman become angry, they’re likely to attribute that anger to her personality—rather than an inciting situation.”
It’s 2022, and “the angry Black woman image is deeply rooted in American’s racist culture and dates back to chattel slavery in the U.S.” Popular culture keeps this trope alive in movies, books, film, and politics. Anger is a human emotion expressed by all. Yet, Black women are painted with this brush too often, which impacts their career opportunities.
I have frustration and anger. I want to do more.
In her consulting work, Cherilynn still hears horror stories. For example, an underrepresented minority woman seeking a raise was told by her male manager, “Your pay is high enough for a woman.” “I don’t have any pride in what I do, “ Cherilynn says in disgust. “I have frustration and anger. I want to do more.”
She says, “I burst with pride when talking about my daughters.” Her daughters have achieved professional success. Cherilynn says with enthusiasm, “They have worked their tails off.” Her oldest daughter, Trier-Lynn Bryant, is a CEO and a former U.S. Air Force combat officer, having held executive positions at Twitter and Goldman Sachs. And Jálynn Castleman-Smith is an operations analyst at a social policy research firm in New York City.
It wasn’t easy growing up with Cherilynn as a mother. She had high expectations for her daughters. She encouraged them to think bigger because she had grown up in a household where good enough wasn’t.
When asked why she was so tough, Cherilynn reflects, pauses, and replies, “I have skinned my knees climbing my mountain.” She thinks about her grandparent’s house burning down several times in Minneapolis due to racism, circa the 1940s. They responded by taking ten years to build a stone house that couldn’t be burnt like their old tar paper houses. The stones were painstakingly carried piece by piece from the Mississippi River. “That’s the type of persistence that I was raised with, ” Cherilynn says.
Bill Green, CEO of Accenture and Cherilynn’s former mentor, taught her a valuable lesson. He said that when you criticize people, it raises their defensiveness. From that moment on, Cherilynn states, “I did a whole paradigm shift at that point, and I stopped criticizing people; now I challenge people.”
The cold winters of Minneapolis have taught her much about life, family and work. Due to back surgery, she prefers warm weather. But she is still that “outdoor girl” who lived in Denver, Colorado. “I am living a life that I love,” Cherilynn says. Anything outdoors suits her because she loves the solitude, whether that be long bike rides or going kayaking. “I’m just out with the water and the birds and the wind and the trees.”
Cherilynn is sui generis. She will not stop trying to make a difference because she knows that life is all about selling--and being seen.
Anthony Price is an entrepreneur, writer and publisher of Mini Books, concise stories for people who are curious about the world.