The Entrepreneur Who Treats Community Like a Business: Calloway Stern Group

When Katy Calloway first started building what would become Calloway Stern Group, a Charleston-based consulting firm that serves small to mid-size nonprofit organizations, she didn’t set out to be an entrepreneur. She was trying to solve a problem — one that she saw up close, in real time, when the pandemic stopped life mid-sentence.

“Until recently, I never considered myself an entrepreneur,” she said. “I started with a business partner … and that’s when I really thought of myself as an entrepreneur.”

Her career has always, in a sense, always been entrepreneurial: launching different initiatives, starting organizations, and navigating constraints that don’t care about mission statements. Most of her work lived in nonprofit spaces, where good intentions collided with limited resources, overextended staff, and the constant demand to do more with less. Then Covid happened. 

“I was working at a group foster home in North Charleston when the pandemic hit,” she recalled, describing that, while being on lockdown, she was managing her own household upheaval with homeschooling, trying to keep her family safe, and watching the nonprofit sector buckle under pressure. 

Calloway Stern Group began as consulting in spirit, but the actual structure became something more specific — nimble and community-rooted. It offers strategic planning, board training, and fractional development services. Calloway Stern Group thinks of itself as a gig economy for nonprofit organizations. “People working in nonprofits, especially in the Lowcountry, don’t make much money,” she explained, “so there was an opportunity to offer these working nonprofit professionals a side hustle in the nonprofit space, as subcontractors.”

Calloway’s idea of a side income paired with mission alignment became a guiding principle. It came with a blunt truth about what many workers were already experiencing: the economy has changed, and “stability” isn’t guaranteed.

“If you don’t have one, get one,” she said. “We are seeing job candidates who have full-time jobs and are applying for another full-time job.”

Calloway is clear that the engine of her company is based on human connection. Her strongest skills are listening, translating needs into actions, and building consensus among people who often don’t have the bandwidth to coordinate. “What’s most effective, especially in a nonprofit, is human to human communications and contact,” she explained. 

That emphasis shapes everything from how she trains boards to how she brings funding into the conversation. Instead of treating nonprofits as isolated islands — each competing for attention and dollars — she works to create networks where organizations can recognize overlap rather than rivalry. “Nonprofits are learning to be less competitive and more collaborative,” Calloway shared, explaining that it’s how “everyone’s going to survive” in the nonprofit sector. 

One of her most candid critiques is about timing and transparency in fundraising. Nonprofits often plan donor outreach around the year-end cycle. She argues that the strongest programs increasingly begin much earlier and depend on honest communication about need. According to Calloway, nonprofits are often conditioned to do outreach at the end of the year. 

“The most effective fundraising strategy is in communicating with your donors,” she explained, encouraging nonprofits to ask themselves whether they have fully communicated their greatest needs to their donors at the beginning of the summer.  Calloway advises nonprofits to be honest about their shortcomings and not feel as though they have everything put together. Funders want to feel like they’re having an impact and are helping solve a problem. Keeping them informed and seeking their help can go a long way, according to Calloway.

Calloway does not romanticize entrepreneurship and has not been without her challenges throughout this process. She invested heavily early on and it turned out to be an epic fail. Her mindset is forward-thinking and she learned to always seek what’s next, and to treat risk as part of progress — not a detour from it. “I’m always looking for what’s next. Where’s the next challenge? Where’s the next idea coming from?”

In the next chapter of her business, she wants to have deeper alignment with the nonprofit funding ecosystem — especially the foundation and corporation giving side — so that the “giving community” and the “receiving community” can move together. 

Calloway Stern Group is building an approach that’s adaptable, collaborative, and deeply human. It’s about refusing to separate purpose from practice, and refusing to treat community work like charity and business like something colder. 

To connect with Katy Calloway, the founder of Calloway Stern Group, for nonprofit consulting services to aid in development, board training, and strategic planning needs, complete the contact form on the website: https://www.callowaysterngroup.com/