This month, we’re shining the spotlight on someone who generally likes to stay behind-the-scenes. Hired 8 years ago on March 29, Cheryl Dean joined the High Hopes team with an enthusiasm that has yet to abate.
Cheryl has taken on a variety of roles here at High Hopes, but the role she currently occupies is that of Director of Development & Marketing.
We managed to snatch a few moments with this often on-the-go director, and we asked her to share about her job, her story, and herself. Let’s get to know Cheryl!
Cheryl and her husband Troy were both born and raised right here in Nashville, Tennessee. Together they have raised four children: Brittany, Bretton, Lucas, and Jakob. The eldest two have left home now, but they remain in Tennessee.
One girl (the oldest) and three boys, all very different in preferences and personality, made life at home quite interesting while they were growing up. With a six-year-old grandson named Huston now thrown into the mix, family life is more fun than ever. “Never a dull moment!” Cheryl says cheerfully.
Cheryl’s office administration expedition began at only 17 years old and has run the gamut as far as experience goes. She started with bookkeeping, payroll, and administrative assistant duties, before going on to be a small business owner for 10 years.
As an active part of the small business she owned with her husband Troy, Cheryl did all things office for them. That meant everything from filing for business licenses to filing business taxes, as well as creating and managing their company website, developing marketing campaigns to grow their business, billing clients, and everything in between.
Cheryl and Troy sold their small business when she decided to go full-time with High Hopes.
Cheryl’s journey with High Hopes began when their youngest was nine years old. She had decided to get a part-time job in order to help pay for the kids’ education. She began applying for jobs, and continued applying for jobs, but for months, nothing panned out. Confused and frustrated, Cheryl kept at it. Finally, she applied for a job at High Hopes, and not long afterward, she received a call requesting an interview.
Excited, Cheryl came to High Hopes and interviewed for a part-time position working under Kristin as an assistant. After the interview, Gail took her on a tour.
Although she had not yet been offered the position, when Cheryl left, she already knew what an important role High Hopes would play in her life. “I called my husband, crying,” she recalls. “I told him, ‘This is where I’m supposed to be.’ I didn’t know what for, or why, but I just knew I was supposed to do something here.”
When she was first hired, Cheryl was going to work seven hours a week as an assistant to Kristin, and as a relief receptionist for two days a week. However, when the need arose for someone to take on the “adventure” that was TEIS billing and documentation, someone had to step up. With her years of experience in insurance and billing, but practically no hands-on training, Cheryl took on the challenge.
These were only the first of many roles Cheryl would go on to fill. “I like the puzzle,” she insists before she recites the lengthy list of jobs she’s taken on for us. “I like to figure it out. So this was a perfect match for me.”
Cheryl’s High Hopes resume alone includes reception, administrative assistant roles for two directors, TEIS billing and documentation, a marketing coordinator position, an office manager position, and more.
“Most people wouldn’t want to come in and do all that, but I like the challenge. Going from this to that to this to that – that’s my pace.” She grins and adds, “It suits me.”
Cheryl has served as the Director of Development & Marketing for 10 months now. Among the various tasks this role entails, fundraising is high on the list. “Development is a cool, nifty word for go raise money,” she jokes with a laugh.
But it isn’t as simple as it sounds. Cheryl’s day can start from the moment she wakes up, checking and responding to emails sometimes before she even leaves the house.
Once in the office, she’s making and fielding phone calls, taking last-minute meetings and business lunches, attending meetings with multiple departments, conducting tours. She also finds, researches, and prepares grants. And that’s all without mentioning how she plans fundraising events to the minute detail, from sponsorships to silverware.
“And then I put on a different hat,” Cheryl continues, and she describes the relationship marketing has with the development team. “Although they’re together, they’re really two separate things.”
Cheryl explains that the majority of our marketing up until now has been primarily related to fundraising, “but as we’re growing, that needs to be teased out and become its own thing. Because it’s marketing for the organization as a whole.”
Cheryl says that she establishes a primary objective for each day, but it’s always subject to change. She equates it to being a batter in baseball, always at the plate. “I feel like I’m constantly swinging.” And she wants to hit every pitch all the way to the fence! Sometimes there are grand slams, and sometimes there are strikes, “but I’m swinging, constantly, at anything that comes our way.”
In fact, Cheryl relates that the biggest challenge she faces in her current role has to do with that home-run mentality of hers. She says the easy go-to challenges like raising literal millions of dollars and balancing between development and marketing are just part of the job. The real challenge lies in facing limitations.
Cheryl says she has learned that she must give herself grace, and permission to not be perfect, which is really difficult for her on a personal level. “That’s the thing,” she says, “I would do anything. But that doesn’t mean I can do everything.”
We take a break for a moment to talk about an upcoming vacation Cheryl has planned. She says it’s just going to be her and Troy and a little cabin somewhere on somebody’s land. That’s her ideal vacation – disconnected from everything, and outside.
It doesn’t matter to her how the outside happens. It could be snow-skiing, hiking, kayaking, going to the beach, or just going for a walk. “I don’t want a computer, I don’t want a television, I don’t want a phone. Just music and nature. I get in my own world for a little while, and forget about everything else.”
Music is big in Cheryl’s world. “It’s kind of ridiculous.” She says her ideal day would be a beautiful Tennessee fall afternoon, taking a nap in the hammock outside, listening to whatever music strikes her mood. She pulls the iPod out of its dock in her office and scrolls through to give us an idea of what she’s listening to.
She rattles off a list of genres from World Relaxation to Classic Bollywood, and starts listing off several diverse artists just from the beginning of the alphabet. “I’m telling you, I like ‘em all. Adele, Jack White, Black Keys, Bob Marley. Just across the board. Cage the Elephant, The Cure, Ella Fitzgerald. Whatever I’m feeling,” she concludes, “I like to have music with it.”
But she never minds coming back to work. Incredibly modest, Cheryl goes on to talk about what makes her stick around.
Obviously, the kids are a huge part of it. “Work’s work,” she says, “so sometimes you’ll have a bad day, things don’t go right, you get frustrated. But –” She gets a little misty as she finishes the thought, “All I have to do is go out there and see. See their little faces. That’s why I’m here.”
Cheryl says her position behind-the-scenes gives her a unique perspective. She gestures to the desk behind her. “I’m behind a computer and a desk with my door closed most of the time. So I can brag on our staff that works with the kids, because I don’t get to work with them. That’s not my gift.”
She sobers and continues, “I want people to know that it’s not me, that it’s the people who are here. It’s the teachers and the therapists that go in, day in and day out, and work with the kids. I couldn’t do that.”
But she knows that her job is important to everyone’s success. “I want to support this. I want to be an encourager. I want to support the ones who are the hands and feet. Not my gift,” she repeats, “and I know that, but I can use my gifts to help.”
And according to her, that’s the most wonderful thing about her job. “I feel like I get to be a part of something that’s not just bigger than me, but that is changing people’s lives forever.” She loves being a part of an organization that invests in these children and families for what she calls a “forever return.”
Cheryl is a huge part of our High Hopes team, and with her intentional leadership and balanced innovation, we’re heading into a very exciting time full of change and growth with confidence in the passionate support of our Development & Marketing Department.