Sophia Shaw’s list of accomplishments is lengthy. She started two companies (first Sophia Shaw and Associates and now PlanPerfect), served as vice president of The Field Museum, president and CEO of the Chicago Botanic Garden, and worked as an adjunct professor at the Kellogg School of Management teaching board governance of nonprofits. Sophia has been devoted to and passionate about supporting the nonprofit community throughout her successful career. As a woman making waves in the male-dominated tech industry, she believes that having a smart, agile strategic plan enables an organization to make significant social impact. When she’s not working with a nonprofit, Sophia is training for a marathon, volunteering with Dare2Tri or Open Water Swim Chicago, or spending time with her husband and grown sons. Take a moment to read more about Sophia below.

1. In three words, describe the essence of your business.
   Nonprofit Planning Software. (Or, for a bit more depth:) Nonprofit-focused. Expert-powered. AI-assisted.

2. What’s one unexpected lesson entrepreneurship has taught you?
   It has reminded me how wonderful collaboration is. Some of the best experiences in my life have come from working with great partners, and this journey with Adam Wolford, my PlanPerfect co-founder, is no exception. Entrepreneurship may seem like a solo endeavor, but the best parts come from building something together.

3. Was there a defining moment when you knew this business was your path?
   When I saw how many nonprofits struggle with strategic planning—not because they lack vision, but because the process is too time-consuming and fragmented. I realized they needed something customized, thoughtful, and kind—software that understands their challenges because it was built by someone who has spent a lifetime in this field. That’s what PlanPerfect is.

4. What’s a sacrifice you made that was harder than you expected?
   The only real sacrifice has been leisure time with my husband. I love what I do, and entrepreneurship has been completely exhilarating, but I do miss the extra downtime together.

5. If you could go back and give your younger self one piece of advice before starting this journey, what would it be?
   Keep doing what you’ve always been inclined to do: build strong partnerships. It’s something I’ve always prioritized, and it has made all the difference. Surrounding yourself with the right people—those who bring different strengths and perspectives—is what makes the journey successful and fulfilling.

6. What’s something about your journey that most people don’t see or realize?
   How personal it is. PlanPerfect isn’t just software—it’s about giving nonprofits the tools to tell their stories, strengthen their missions, and ultimately make the world kinder and more just.

7. What fuels you on the tough days?
   Knowing that nonprofits do some of the hardest, most important work in our society—and they deserve better tools. Plus, my co-founder, my family, and my endurance sports mindset keep me going.

8. What does success look like to you beyond the bottom line?
   Nonprofits thriving because they finally have a planning tool that works for them. Seeing their impact grow because PlanPerfect made strategic planning easier is the real win.

9. Who has been your biggest supporter or source of inspiration along the way?
   My co-founder, Adam Wolford, has been an extraordinary partner. But also, my husband, my sons, and close friends always remind me why this work matters.

10. What’s one thing people can do today to better support women-owned businesses?
    Trust in us. Invest in us. I’m very proud to be a late-middle-aged woman who has become a tech entrepreneur. It’s funny that an older woman would even have to think it’s funny to start a tech company—but that’s still how it is. The best way to support women-owned businesses is to challenge those assumptions, recognize expertise wherever it exists, and back the businesses that are building something meaningful.

Photo Credit: Heather Donlon