Hearts for Service

When Wander Bailey walked into the City of Chesapeake's Department of Human Services in 2008, she was just a temporary office assistant with a willingness to help wherever she could. What she didn't know then was that those first days would spark a lifelong calling.

"Even back when I was a temp, I knew this was where I belonged," Bailey remembers with a smile. "This department was all about helping people in need but also supporting one another in the process. I liked that."

By 2011, Bailey secured a permanent team position, becoming a reliable member who willingly took on various roles to assist citizens in need.

"I tried to learn everything I could," she says. "From helping a family keep their lights on to assisting with an application for benefits, I learned very quickly why this work is so important."

Nearly 14 years later, Bailey's dedication was recognized in a big way. In February 2025, she was promoted to Benefits Program Supervisor.

Bailey points out that she was never alone on her career path and credits early mentors, like former Chief of Benefits Harry Cromer, who encouraged her to learn as much as possible. "He pushed me to gain as much knowledge as I could. That advice is what made me build this career."

Now, Bailey is focused on leading with the same compassion and commitment she's always admired. She strongly believes the success of the department is all about the team.

"I wish people could see the effort that goes on behind the scenes," she says. "Our Intake staff are incredible. They're understaffed, they face mountains of applications, tight deadlines, and they do it all while managing their own families and personal challenges. I see how hard they work and how much they care. I want them to know they're valued."

She also speaks with gratitude about the leadership of Director Pamela Little-Hill. "She's the kind of leader who leaves boxes of free produce for people, she provides clothing and other necessities in our food pantry, always leading by example and going the extra mile."

For Bailey, the work is personal. As a breast cancer survivor, she's acutely aware of how quickly life can change. "It doesn't take much, a diagnosis, a job loss, an accident. Any of those things can happen and suddenly, your whole world is turned upside down. That's why I try to see every client, every family, as someone who could be me or someone I love."

Her message is simple, look at your community with compassion.

"Behind every application, there's a human," she says. "Families just like ours, people who never thought they'd be in that position. Stop judging and start seeing each other for who we are, just people doing our best to find a way and make progress."

At the core of Wander Bailey's career lies her commitment to being present for others, uplifting them during life's most challenging moments.

"I'm thankful for my team and I want to remind people that you don't have to work here to make a difference. Anyone can be of service to others, if they make that choice."

For more information about Chesapeake's Human Services Department, visit: CityOfChesapeake.net/HumanServices