Disruptors. They are the few and the fierce. In our series, Leading between the Lines, we have the opportunity, and the pleasure, of meeting with some of South Florida’s most dynamic female business leaders, ones who are disrupting their industry, approaching things in a new way, solving new problems, and effectively pushing the status quo into a new frontier. We want to learn about their journey, what it really takes, what they’re actually up against, and how it feels each step along the way.

Meet Joe Ann Fletcher, CEO of Dress for Success Palm Beaches, one of the 140+ affiliates of the international nonprofit organization that empowers women to achieve economic independence by providing a network of support, professional attire and the development tools to help women thrive in work and life. Since its founding in 1997, Dress for Success has helped more than 1 million women work toward self-sufficiency. 

For more than two decades, Joe Ann Fletcher has demonstrated outstanding nonprofit leadership within our South Florida community. Among her various roles over her 20-year career, she served as Vice President of Programs and Operations for HGH Education Foundation in West Palm Beach and CEO of St. Laurence Chapel Homeless Day Shelter in Pompano Beach, before eventually joining Dress for Success Palm Beaches in 2022 as the Executive Director and eventually rising to CEO of the organization, which today serves three counties- Martin, Palm Beach, and Broward.

Read our full interview with Joe Ann, to learn why she’s chosen to build a purpose-driven career, how she’s leading Dress for Success Palm Beaches through a rapidly evolving world, and why this organization is about so much MORE THAN THE DRESS!

For the past two decades, you’ve built an incredible career in nonprofit management, and today, serve as the CEO of Dress for Success Palm Beaches, overseeing Martin, Palm Beach, and Broward Counties. What initially drew you to the nonprofit sector, and what convinced you early on that this was the right long-term path? 

From a young age, I felt a strong purpose in helping others, particularly women. Volunteering as a Candy Striper from age 13 to 18 was my first volunteer service experience, where I learned the power of empathy, connection, and encouragement. 

I spent countless hours with patients, offering companionship, a listening ear, and words of comfort. I learned how valuable a simple conversation, or a few words of encouragement could be. This early experience profoundly impacted me, planting the seeds for my lifelong commitment to helping others. It also helped shape my understanding of empowerment through words of encouragement. 

As I continued my journey into nonprofit work, I realized that empowering women is a unique and powerful calling. Women have faced many societal, economic, and personal challenges throughout history. I have seen how crucial it is to provide women with the tools, resources, and, most importantly, the belief in themselves to overcome those challenges. My passion for this work has only deepened over the years. The day I was offered the position at Dress for Success, I knew it was an ideal fit. 

Nonprofit work is a gratifying field, though not without its challenges. It requires immense dedication, creativity, and persistence knowing that resources are often limited, yet the need is great. 

What has been your proudest achievement thus far, and why?

Throughout my career, the most profound lesson I’ve learned is that true empowerment comes from within. My role has always been to provide external support and encourage women to tap into their inner strength, build resilience, and realize their potential. 

It’s a journey of supporting women through their challenges and helping them believe in themselves enough to take the steps toward the future they deserve. 

At Dress for Success, the services, programs and resources we provide require raising funds, getting new donors, maintaining funders, recruiting volunteers, and community leaders. It takes a lot of passion, dedication, and multitasking to manage all these responsibilities; however, each time I accomplish a task, knowing how it will impact others, I feel incredibly proud and fulfilled. Empowering women and seeing them excel- that is my proudest achievement. 

What are some of the challenges you’ve faced in your career and what have you learned from them? 

Throughout my career in nonprofit management, I’ve faced numerous challenges and setbacks, many of which have been valuable learning experiences. 

One of the most significant challenges has been navigating the complex nature of funding in the nonprofit sector. Securing sustainable financial support is an ongoing struggle, especially when funding priorities change or donor interest fades. 

Another challenge has been managing growth while maintaining the quality of our services and personal touch. As Dress for Success Palm Beaches expands its reach, the demand for services grows, but I still must ensure that we continue to meet the needs of every woman. Over the years, I have learned the importance of balancing expansion and quality of service. I also learned the value of empowering my team to take ownership of key responsibilities, which leads to stronger collaboration and more efficient operations.

Regarding personal growth, one of the areas I've improved on the most is communication and leadership. Early in my career, I focused more on the technical aspects of nonprofit management, such as budgeting, programming, and operation. Over time, I realized that I also needed to keep the entire team inspired and motivated about their roles. I’ve become much more purposeful in providing clear, open communication among staff and volunteers knowing that a motivated, well-supported team impacts the organization's success.

What has surprised you most on your career journey?

What has surprised me the most as a nonprofit CEO is the constant balancing act between passion for the mission, raising funds, grant writing, and running the organization. 

The reality of managing finances, navigating bureaucracy, ensuring sustainability, and satisfying the needs of donors, clients, and staff can be incredibly overwhelming. And yet, every time I manage to navigate a challenge or achieve a big win, I am invigorated and the passion I have for this mission propels me to face it all again.

Another surprising aspect is how much time is spent on building relationships. Fundraising isn't just about asking for money; it’s about cultivating relationships with donors, volunteers, and community leaders- at that takes a lot of time and attention to detail. Relationship-building often becomes as critical as direct service work because donors are needed to maintain those vital services.

Every leader faces moments of uncertainty, doubt, or fear. What scares you and how are you navigating that fear?

One of my biggest fears as a nonprofit CEO is the financial stability of our organization. Unlike for-profit businesses, nonprofits rely heavily on donations, grants, and fundraising efforts, which can fluctuate- sometimes drastically.

I have faith that we will be successful, but ensuring we have enough funds to continue programming or meet payroll is always top of mind for me. This is why fundraising is such a priority. I always try to have a steady revenue stream, so I don’t have to worry. 

Today, my biggest challenge is raising enough funds for our upcoming relocation project while maintaining income for programs and payroll.  Finding new funding sources is always challenging, but I’m unrelenting in networking and developing new relationships. 

What influences and inspires you?

I am forever inspired by the people we serve and watching each woman become more empowered and economically self-sufficient. The small victories and moments of transformation fuel my soul. I love our tag line “More than the Dress” because it truly encapsulates the full scope of transformation that takes place here at Dress for Success. 

Seeing the women come in looking down and depressed, then leave smiling with their heads held high is inspiring. But seeing how that confidence translates into action that changes their lives is what really motivates me.  The feedback and kind words from clients, volunteers, board members, and staff propel me to keep going and keep making a difference.

Talk to us about the tag line “More than a Dress”. What is the real scope of impact Dress for Success is making?

Dress for Success is addressing many challenges faced by women in our community. 

First and foremost, it is providing an uplifting experience that helps a woman realize her self-worth. The organization is positioned as a vital career resource, offering each woman the development tools to prepare her for the workforce – and then, of course, ensuring she’s looking her best and dressed for success. 

The caring for each client goes deep. We track her progress throughout the job hunt and even once she’s employed. We also support her continued development through our Professional Women’s Group which provides ongoing coaching and guidance to support career advancement. 

What is unique about Dress for Success is that we’re solely focused on women, with programming and services designed to address the unique needs and challenges that come with empowering women. It’s a delicate and layered approach of building confidence from the inside-out.

The most common misconception is that we simply provide clothing. But the reality is that we are MORE THAN THE DRESS– with a robust schedule of job readiness programming and training featuring leading experts, as well as a community of dedicated morale-boosting volunteers from the business world who mentor and share their experience, wisdom, and advice. 

For those just learning about Dress for Success, what is the one key takeaway you want our readers to remember? 

While we appreciate the community response when it comes to donating clothing, financial support is vital and enables us to continue the comprehensive work we do and maintain the caliber of programming that leads to meaningful impact. 

What does the future of Dress for Success look like? How is the organization evolving to address new challenges?

We are striving to meet the needs of a changed work landscape. 

When it first was established, Dress for Success was all about “suiting”. In this post-COVID era, working remotely has become more common which begs the question: should we be providing the same professional attire for the women we serve? 

In today’s business world, a suit may not necessarily be the best option, even for an interview, especially here in South Florida, where acceptable workplace fashion tends to be more casual. As the world gets more digital, job readiness and skill building programs need to adapt to stay relevant and ensure these women are set up for success in today’s job market. So, we are striving to stay savvy and address shifts like these.

We’re also focused on the recruitment of a younger generation of volunteers and future philanthropists. Volunteers are vital to our operations – we only have 4 paid staff and rely heavily on our volunteers. They are the lifeblood of Dress for Success, serving as personal stylists for clients, mentoring and coaching, managing our inventory, and helping us raise funds. We’re exploring ways to attract and engage the younger generation who will become our future supporters. One of the ways we are achieving this is through our Y.E.S. initiative – Young Executives for Success. 

Overall, it’s critical we evolve and remain relevant for the women we serve as well as for our volunteers and supporters.

What advice would you give to business leaders seeking to get more involved in philanthropy within their community?

Philanthropic involvement can be a great way to expand brand awareness and grow your business. The key is to identify organizations that align with your corporate culture and values. Then, do a deep dive into learning more about those organizations. Charity Navigator is a great resource and provides information not only on the mission of a charity but also rates its performance and accountability. 

Next, consider your level of involvement. There are many ways to get involved beyond donations and sponsorships.  Volunteering to serve on a board, volunteering to serve within the organization’s programming, or supporting fundraising events and initiatives are all great ways to hone leadership skills, build meaningful relationships with other leaders in the community, and make an impact by serving those in need. For many of our supporters, the impact is most rewarding.

Obviously, our mission is to empower women and typically that is a shared priority of our supporters. But, as many know, the impacts of empowering a woman and helping her to become economically independent go far beyond that individual. When you empower a woman, you uplift her family and, in turn, her entire community!