Ravi Cooper is a Charlottesville area CEO who leads United Way of Greater Charlottesville, an organization that has grown from $2 million to nearly $19 million in revenue since she stepped into the role in 2018. She joined Virginia CEOs that same year, and she credits her Roundtable peer group with shaping almost every major decision since.
How did United Way of Greater Charlottesville grow from grant-maker to community builder?
When Ravi arrived, United Way of Greater Charlottesville worked from the traditional model: raise money through workplace campaigns, then redistribute it through roughly 25 grants a year to local nonprofits. Today the Charlottesville-based organization runs its own programs directly, with a staff that has grown from 8 or 10 people to almost 40.
The scholarship program alone serves about 520 children a year with full-day, full-year childcare support. The organization also runs workforce training for early childhood educators, small business grants through local chamber and economic development partnerships, homeownership programs with Habitat for Humanity, and transportation assistance that helps people rebuild credit and get to work reliably.
This year the organization is on track for $3.3 million in private philanthropy, up from just over $1 million a few years ago. It also secured a state grant of about $13 million from the Virginia Early Childhood Foundation and a $3.4 million Head Start grant, its most recent win.
What did Ravi learn stepping into a CEO role for the first time?
Ravi wasn’t a first-time executive when she took the United Way job. She had spent years in leadership roles, including a stint helping build a $20 million YMCA project in Charlottesville. But she hadn’t run an organization as CEO before, and she says that role comes with challenges no amount of prior experience fully prepares you for.
That’s where her Roundtable came in. Early conversations with her peer group introduced her to the Entrepreneurial Operating System, the management framework from the book Traction. Adopting it gave her organization the structure to set goals, track KPIs, and scale without losing cohesion. Group members also pointed her toward the HR platform she still uses today.
She pushed back gently on the idea that nonprofit CEOs need a nonprofit-only peer group. In her experience, about 95 percent of what comes up in a business roundtable applies whether you’re running a nonprofit or a for-profit company. Staffing, personnel decisions, difficult conversations: those challenges don’t care what kind of tax form your organization files. What she was looking for, and found, was a for-profit lens on nonprofit work.
What was Ravi’s first Virginia CEOs Roundtable meeting like?
Ravi still remembers her first meeting. She hadn’t been in a group before where members talked as openly about their personal lives as their professional ones, and it caught her off guard. She left having shared childhood stories she hadn’t talked about in years, feeling more exposed than she expected with people she barely knew.
That openness set the tone for the group. Six years later, only two original members remain, but the same directness is still there.
How do you grow fast without losing people?
Rapid growth brings its own problems. Ravi’s biggest challenge over the past 18 months has been keeping teams connected as the organization scales. When senior leaders move fast, mid-level managers and coordinators can get left behind, and cohesion starts to slip. She’s been told this is a normal growing pain for organizations expanding as quickly as hers has. Knowing that doesn’t make it easy, but it does make it easier to solve.
What is Ravi most proud of?
Over the past four years, United Way of Greater Charlottesville has put $50 million back into early childhood care in central Virginia. The organization now works directly with UVA’s president, the Charlottesville city manager, and the local school system on community initiatives. The team set a goal to help 1,800 families reach financial stability. They’ve already reached 1,500, with a year still to go.
How does a Charlottesville CEO stay sharp and avoid burnout?
Ravi is deliberate about unplugging. Daily walks, meditation, family time, and a six-month leadership fellowship through Darden all factor into how she avoids burnout. She’s built the same flexibility into her organization’s culture, redesigning the PTO system so staff can take the time they need without guilt, as long as the work gets done.
Her leadership style traces back to her years at Whole Foods, where she started working at 19 and spent 12 years in leadership roles shaped by John Mackey’s conscious capitalism philosophy. That experience taught her to treat every team and department like its own small business, giving people real ownership instead of managing from the top down.
What’s next for United Way of Greater Charlottesville?
United Way of Greater Charlottesville just took on 11 new counties stretching from Fredericksburg to the Northern Neck. The organization is also opening its first childcare lab school in partnership with UVA’s School of Education, funded by a $43 million gift, the largest in the school’s history. A new pilot program called ALICE in the Workplace will partner with major local employers to support low-income working populations and reduce turnover tied to childcare and transportation gaps.
A fun fact about Ravi
Ravi grew up in Sonoma County, California. At 15, she started her own business selling edible flowers, with help from her father’s organic produce company. Her first customers included the White House and Wolfgang Puck’s restaurants in Los Angeles.
Why does Ravi value her Virginia CEOs Roundtable?
Ravi calls her Roundtable a financial and time investment that’s paid off many times over. Six years in, she still can’t imagine running her organization without it.
She also just finished a year as Rotary District Governor, a four-year commitment she says she took on despite already having plenty to do. Ravi believes she’s the first sitting CEO in her district’s history to hold the role while running an organization full time. She visited all 51 clubs across the district, logging 75 nights in hotels along the way.
A big thank you to Ravi for taking the time to sit down with us and share her story. Her openness about the wins, the growing pains, and everything in between is a great example of the vulnerability and the openess that makes a great VACEOs member.
The Virginia CEOs Stories series highlights the people leading Virginia’s most impactful companies and organizations. From Charlottesville to Hampton Roads, Richmond to Northern Virginia, the series shares the real challenges, decisions, and lessons behind each leader’s journey, and shows what happens when CEOs commit to growing alongside their peers. If Ravi’s experience resonates, whether it’s the pace of growth, the search for the right peer group, or the balance between running an organization and staying grounded, you’re in good company.
Want to connect with Ravi, learn more about United Way of Greater Charlottesville, or explore what a VACEOs Roundtable could look like for you? Reach out through Virginia CEOs. We’d love to introduce you to the community behind the stories.
