Katy Sides Women in Business Award 2026

Katy Sides

Hollingsworth Funds

Director of Learning

Greenville

Katy Sides joined Hollingsworth Funds in 2017 and serves as director of learning. She manages the foundation’s learning agenda, aligning philanthropy, real estate, and investments with its mission, while overseeing communications and evaluation. A Hull and Riley Diversity Leaders Fellow, Sides is an avid volunteer. She serves as the Rose Ball’s beneficiaries chair, secretary of Greater Good Greenville, on the Hope Ball Committee, and previously in various leadership roles for the Junior League of Greenville.

What makes you an effective leader? Your greatest strength? What are you still working on?

My greatest strength is identifying individual gifts and empowering others through strategic delegation. By setting clear expectations and trusting my team to lead, I foster an environment where everyone can thrive. I am still working on quieting my inner critic; I strive to view my own contributions with the same grace and objectivity I extend to my colleagues, learning that effective leadership begins with self-compassion.

What one thing have you learned that has served you well over the years?

I have learned to embrace crucial conversations the moment they arise. While Southern women are often conditioned to hold back or doubt their own value, I’ve found that silence only allows concerns to fester. By speaking with kindness and confidence, I ensure small friction points don't grow into larger obstacles. Addressing issues early and staying true to my perspective has served me well, fostering healthier, more honest relationships.