Women’s History Month Leadership Series
This Women’s History Month, we’re proud to spotlight the voices of women leaders in our community who are shaping workplaces, building teams, and making a lasting impact.
We invited a group of female leaders to partner with us and share their personal leadership journeys: how they got started, the lessons they’ve learned along the way, and the advice they would offer to the next generation of women in leadership.
Each story offers a unique perspective, but together they highlight a common theme: leadership isn’t one-size-fits-all. It’s built through experience, resilience, and a commitment to lifting others up along the way.
We’re closing out our Women’s History Month Leadership Series with Jenni Kirby’s story, a perspective shaped by persistence, collaboration, and a commitment to building community.
As the founder of Crossroads Art Center, Jenni has learned that leadership isn’t about having all the answers—it’s about creating opportunities, trusting your instincts, and empowering others to succeed. Her journey offers lessons for women in business and leadership at every stage of their career.
Leadership, to me, means creating opportunities for others and building an environment where people can succeed. Early in my career, I thought leadership meant having the answers and making the decisions. Over time, I realized it is much more about listening, problem-solving, and bringing people together to find the best path forward.
As a woman in business, especially when I started out, I learned quickly that you sometimes had to prove yourself more than others did. That experience taught me persistence and confidence in trusting my instincts. It also taught me the value of collaboration. Some of my best ideas and solutions have come from listening to the people around me—my staff, the artists we represent, and the friends I jokingly call my “Board of Directors.”
Leadership has also meant creating a space where people feel welcome and respected. At Crossroads Art Center, that was always a priority for me. I wanted to build a gallery that wasn’t intimidating or pretentious, but a place where artists could grow and collectors could feel comfortable discovering art.
Over the years, my definition of leadership has become simpler: work hard, treat people fairly, trust your gut, and always keep learning. A good leader doesn’t just build a business—they build a community.
Advice for Future Female Leaders
If I could share a few things with the next generation of women in business, the first would be trust your instincts. Your gut is usually right, even when others may question your ideas or your direction. Confidence grows over time, but learning to trust yourself early makes a huge difference.
Second, be persistent. Running a business is rarely a straight path. There will always be obstacles, unexpected problems, and moments where you wonder if you made the right choice. The key is to keep moving forward and keep figuring things out. Most successful people didn’t have all the answers—they just didn’t quit.
I would also encourage women to build their own support network. I have what I jokingly call my “Board of Directors,” a group of trusted friends and colleagues I bounce ideas off of when I’m trying to solve a problem or see a situation from a different perspective. You don’t have to figure everything out alone.
Another important lesson is don’t be afraid to pivot. The world changes, businesses change, and sometimes your plans have to change too. When COVID hit, we had to quickly shift to online sales to keep Crossroads Art Center alive. Being flexible and open to new ideas is essential.
And finally, create the opportunity if it doesn’t exist. That’s exactly why Crossroads Art Center was started—to give artists a place to show and sell their work when traditional galleries might not have given them that chance.
If you find yourself at a crossroads in your career, remember that those moments are often where the biggest growth happens. Take a deep breath, trust your judgment, surround yourself with good people, and move forward with confidence.
Lessons Learned
If I could go back and give my younger self a few pieces of advice, there are three things I would say.
First, trust your instincts sooner. Early on, I sometimes second-guessed myself or waited for others to confirm what I already felt was the right decision. Over the years I’ve learned that your gut is often your best guide in business. Experience helps sharpen that instinct, but learning to trust it earlier would have saved me a lot of time and worry.
Second, surround yourself with good people and ask for their perspective. No one builds a business alone. Having a trusted group of people, you can bounce ideas off of—people who will challenge your thinking and offer honest feedback—makes all the difference. My unofficial “Board of Directors” has helped me look at problems from angles I might not have seen on my own.
Third, be willing to adapt and pivot when necessary. Business is constantly changing, and sometimes the path forward looks very different than what you originally planned. The ability to adjust, learn new things, and move in a new direction when needed is what keeps a business alive and growing.
Looking back, the biggest thing I’ve learned is that leadership and entrepreneurship are really about persistence and problem-solving. You roll the problem around from every angle, figure out the best solution you can, and keep moving forward.
Jenni’s story reminds us that leadership is about more than titles or business success—it’s about creating opportunities, lifting others up, and building a community where people can thrive. Her journey highlights the power of persistence, collaboration, and trusting your instincts, showing that meaningful leadership grows from both challenges and successes.
As we conclude our Women’s History Month Leadership Series, we celebrate all the women leaders who are shaping workplaces, inspiring teams, and leaving a lasting impact on their communities. Their stories remind us that leadership comes in many forms, and that each of us has the power to make a difference.
About the Author:
Jennifer Kirby is the Owner of Crossroads Art Center in Richmond, Virginia, one of the largest and most
dynamic art centers on the East Coast, representing hundreds of local and regional artists. A passionate arts advocate and entrepreneur, she focuses on creating innovative opportunities for artists while building meaningful community partnerships. Her leadership centers on sustainability, collaboration, and elevating the visibility of working artists.
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