Business / St. Louis Business 500: Q&A with Dr. Cheryl Watkins, YWCA Metro St. Louis

St. Louis Business 500: Q&A with Dr. Cheryl Watkins, YWCA Metro St. Louis

Insights from YWCA Metro St. Louis’ President and Chief Executive Officer.

Watkins is leading what’s billed as the region’s oldest and largest women’s advocacy agency. For women facing hardship, the YWCA supplies essential resources, such as transportation, food, rent and utility assistance, and child care. “I read the stories of the women we serve who have escaped violence and poverty and worked their way through therapy and our programs, and have come out on the other side able to support themselves and change the course of their family’s life,” she says. “Inspires me every time.”

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Dr Cheryl Watkins
2026 QUESTIONNAIRE

PROFESSIONAL ACCOMPLISHMENTS & OPPORTUNITIES

What has been your/your company’s most significant success over the past 12 months? We are the oldest and largest women’s advocacy agency in our region (121 years!), and we have integrated, aligned, and continuously improved our services to provide the greatest impact for our clients. For example, a woman who has become unhoused as result of sexual/domestic violence can heal with us and achieve a level of economic stability that leads to home ownership. While she trains for a new job or even entrepreneurship, her children have access to high quality childcare and early education. And, we are the only agency in the region that provides essential wraparound services that support and sustain our clients while they’re in our programs—transportation, food, rent/utility assistance, childcare—so they can complete the program and move from striving to surviving to thriving. The services we provide to our clients are transformational. We were honored to receive YWCA USA’s Association of Excellence Award for Mission Impact in the Field of Women’s Empowerment, and were awarded the National Program of Excellence Accreditation (2022-2027) by the National Head Start Association for our Head Start program. Most recently, we received the FOCUS St. Louis What’s Right with the Region award for Demonstrating Innovation for our Successful Pathways apprenticeship that solves for lack of childcare professionals and puts individuals on a path to a professional career in Early Education. The program is now available to all community childcare providers!

What has you most excited about the future of your company or industry? Our programs truly empower women and families—we can move a family from crisis to stability to healing to self-sufficiency. The best programs cannot work if clients are unable to complete them. Our wraparound services, provided at no charge, support and sustain our clients so they are able to successfully complete our programs. These services remove the most common barriers to success: food assistance, housing, childcare, transportation, and rent/utility assistance.

If you could change one thing about your industry, what would it be and why? Erase the need for human services agencies. Provide every woman—every human—with the opportunity to earn a living wage, and create safe, stable, and affordable environments in which we and our children can thrive. Why? It’s our human right.

What’s the toughest business challenge you’ve had to overcome? Two challenges rise to the top: Funding and talent acquisition. We are actively working to reduce our dependence on government funding, and to inspire all categories of businesses in our region to support our programs by providing data around ROI for their support. Non – profits cannot afford to pay the highest salaries, though we are charged with finding great talent that is committed to doing the hardest work. Despite these challenges, I’m proud to say we are committed to paying competitive market wages and have attracted an excellent team at YWCA. This is how we have been able to grow stronger and provide the services that truly impact our clients and transform lives.

What’s a risk you took in business that didn’t pan out—but taught you something valuable? I led a large multi-corporate, interdisciplinary team tasked with creating a new business unit for a global organization and I jumped at the chance to take charge of the project—but as we fully explored the challenge, we concluded that the project should not move forward. This taught me that even though this seemed like a great project to lead, accepting the challenge without full clarity on what organizational success (and cost) looked like did not set us up to succeed.

What advice would you give to the next generation of St. Louis entrepreneurs or leaders? To be driven by success is laudable, but also be driven to serve others.


MENTORS & PEERS

What is a key strength of the St. Louis metro area business environment? I am a co-chair of the Investor’s Circle for Greater St. Louis, Inc., and I can assure you that business in our region has a collegial spirit – we want the region to succeed. Also, it is remarkable that our region has attracted not one, but four innovation districts.

What is one thing you would change about the St. Louis metro area business environment? We must create an environment that celebrates critical and creative thinkers who truly reimagine problem-solving as a team effort—across the spectrum of corporate, nonprofit, philanthropic, and economic development. No single entity can provide the solution to the issues that face our community. We have to work together and share our strengths.

Who is the most interesting under-the-radar/emerging business leader in St. Louis? La’Crassia Wilderness, founder of Butterlove, started her business in her dorm room to heal herself. And Ciara Imani May, founder of Rebundle, built her business to address a need and developed a product that is effective and sustainable. Keep an eye on these young African-American entrepreneurs who continue to impact their community—they are two to watch.

Who in your company (or industry) deserves more recognition for their impact? All the employees who provide direct services to women and families at YWCA deserve more recognition and appreciation. They truly change the lives of thousands of women and families in our region each year—our crisis team helps survivors find safety, stabilization, healing, and self-sufficiency. And don’t forget about our early education professionals. Is there a job more important than caring for and teaching our children?

What’s a local organization, nonprofit, or initiative that more people should know about—and why? YWCA Metro St. Louis! Although we’ve raised our profile significantly over the past few years, it is still an ongoing challenge to get people to differentiate YW from YM (also a stellar organization). I also want to give a shout out to YWCA USA, who is tirelessly advocating for our rights in Washington.


BACKGROUND

Where were you born? Chicago

What educational degrees do you hold, and where were they earned? Bachelor of Arts, Biology – Fisk University; Doctor of Podiatric Medicine, Surgery – Rosalind Franklin University of Medicine and Science; Master of Business Administration – Northwestern University – Kellogg School of Management

What was your first job, and what did you learn from it? I worked as a cashier at my uncle’s shoe repair shop at 13. That was my first exposure to entrepreneurship, and I also learned to count money – without a calculator!


HOBBIES & INTERESTS

What’s your hobby/passion? Travel!

What is one book you think everyone should read (or podcast everyone should listen to) and why? I highly recommend Killers of the Flower Moon: The Osage Murders and the Birth of the FBI by David Grann. It’s a reminder of the tragic consequences of dehumanization and the importance of diversity and inclusion.

What do you do when you’re feeling stuck or uninspired? I read the stories of the women we serve who have escaped violence and poverty and worked their way through therapy and our programs, and have come out on the other side able to support themselves and change the course of their family’s life. It inspires me every time.

What would people be surprised to learn about you (fun fact)? I’m an RVer! Really! It’s a very nice RV, and it’s a fantastic way to see our beautiful country.


2025 QUESTIONNAIRE

PROFESSIONAL ACCOMPLISHMENTS & OPPORTUNITIES

What has been your or your company’s most significant success over the last 12 months? We’ve won some meaningful awards over the past year, including What’s Right with the Region and YWCA USA’s Association Excellence Award for Mission Impact in Women’s Empowerment. But I think our most significant success is that we’ve achieved three consecutive years of budget growth since I came on board in 2021. We’ve grown our budget by 20 percent since I got here. We’ve also reimagined and rebuilt our core services. We have plans to grow our Housing & Crisis Services, our Early Education Program (we’re opening new schools with our Innovation District Partners, Cortex and 39 North), and we’ve significantly improved CREED, our work readiness program.

What has you most excited about the future of your company or industry? We are the oldest and largest women’s advocacy agency in our region, and what excites me most is that our services are integrated, aligned, and continuously improved to provide the greatest impact for our clients. For example, a woman who has become unhoused as result of sexual/domestic violence can heal with us and achieve a level of economic stability that leads to home ownership. While she trains for a new job or even entrepreneurship, her children have access to high quality childcare and early education. And, we are the only agency in the region that provides essential wraparound services that support and sustain our clients while they’re in our programs—transportation, food, rent/utility assistance, childcare—so they can complete the program and move from striving to surviving to thriving. The services we provide to our clients are transformational.

If you could change one thing about your industry, what would it be and why? This one is easy: erase the need for Human Services agencies. Provide every woman, every human, with the opportunity to earn a living wage, and create safe, stable, and affordable environments in which we and our children can thrive. Why? It’s our human right.

What’s the toughest business challenge you’ve had to overcome (excluding the pandemic) and why? Funding is always challenging, and so is talent acquisition. Non-profits cannot afford to pay the highest salaries, though we are charged with finding great talent that is committed to doing the hardest work. Despite these challenges, I’m proud to say we are committed to paying competitive market wages and have attracted an excellent team at YWCA. This is how we have been able to grow stronger and provide the services that truly impact our clients and transform lives.


MENTORS & PEERS

To whom or where do you go for sound business advice? I have myriad sources: trusted business journals and individuals who are traveling along a similar career and leadership path. I pay attention to their successes and their failures, knowing there is much to learn from both.

Do you have a business mentor? If so, who and why? I have many mentors! Everyone brings value from a different perspective.

What piece of advice has had the most significant impact on your career? Winston Churchill said, “Success is not final and failure is not fatal. It is the courage to continue that counts.” Recognize every opportunity to learn, whether a situation is good or bad…it, too, is a lesson.

If you could have dinner with any two area business leaders, who would you choose and why? I would love to share a meal with Katie Lee, preferably at Katie’s Pizza & Pasta Osteria! Her personal and professional journey is inspiring, and I’ve enjoyed watching her grow her business from brick & mortar to include expansion and distribution. I would also love to sit down with Kory Mathews, CEO and Executive Director of AMICSTL, to talk about innovation and its impact on our region. Innovation drives progress, attracts top talent, and impacts everyone in our community.

Who is the most interesting under-the-radar/emerging business leader in St. Louis and why? La’Crassia Wilderness, founder of Butterlove, started her business in her dorm room to heal herself. And Ciara Imani May, founder of Rebundle, who also built her business to address a need and developed a product that is effective and sustainable. Keep an eye on these young African American entrepreneurs—they are two to watch!

What is one thing you would change about the St. Louis metro area business environment and why? I believe we need to create an environment that celebrates critical and creative thinkers who truly reimagine problem-solving as a team effort, across the spectrum of corporate, nonprofit, philanthropic, and economic development. No single entity can provide the solution to the issues that face our community. We must work together and share our strengths.


BACKGROUND

Where were you born? Chicago

What was your childhood aspiration? As a child, I wanted to be a physician and a mom, and I’m proud to say I achieved both!

What was your first job, and what did you learn from it? I worked as a cashier at my uncle’s shoe repair shop at 13. That was my first exposure to entrepreneurship, and I also learned to count money—without a calculator!

What educational degrees do you hold, and where were they earned? I earned a BA in Biology at Fisk University, I earned my MD at Rosalind Franklin University of Medicine and Science in Chicago, and I earned my MBA from the Kellogg School of Management at Northwestern University.


HOBBIES & INTERESTS

If you were not in your current profession, what would you be doing and why? I would travel the world and experience other cultures and ideas. I am a lifelong learner, and I know I could share what I’ve learned to benefit others.

What is your favorite St. Louis-area restaurant, and what do you typically order there? I am a big fan of Oceano Bistro. I love the mango spinach salad and lemon crab risotto. I also love the New York strip at Ruth’s Chris Steak House.

What is one item you recently crossed off your bucket list? Running a large, impactful nonprofit.

What is one book you think everyone should read (or podcast everyone should listen to) and why? I highly recommend Killers of the Flower Moon: The Osage Murders and the Birth of the FBI by David Grann. It’s a reminder of the tragic consequences of dehumanization and the importance of diversity and inclusion.

What’s your hobby/passion? Travel. I am very much looking forward to my upcoming trip to Italy.

What would people be surprised to learn about you—a fun fact? Believe it or not, I’m an RV-er. It’s a very nice RV and a fantastic way to see the country.

What is your go-to karaoke song? I have to choose just one? I love Chaka Khan, so I’d be up for any of her hits.