Meet Winnie Kennedy

By Henna J. Shah

Delightfully Chaotic spoke with Winnie Kennedy, a humanitarian leader and founder and CEO of Rosarit Girl Child and Humanity Foundation, a non-governmental organization focused on empowering marginalized youth, especially young girls who have dropped out of school, are pregnant, or are orphaned. Kennedy also is a leader of initiatives such as Youthsphere, an AI-powered platform that connects youth-reported community challenges to registered non-governmental organizations for solutions, EduWealth, a Defi-based app focused on ending student poverty through skill tokenization, peer-lending, micro-grants, and Girls In Diplomacy, a training ground to raise the next generation of female global voices.

Winnie, can you share a bit about your personal background and what led you to humanitarian work?

I grew up surrounded by stories of resilience and sacrifice—my grandmother Rose Arit, whom the foundation is named after, was a quiet yet powerful woman who nurtured others with unwavering strength. Her legacy shaped my empathy early on. But it wasn’t until I worked directly with vulnerable girls in under-resourced communities that I felt the deep call to commit my life to advocacy. Humanitarian work, for me, is not a profession. It’s a ministry.

What inspired you to create the Rosarit Girl Child and Humanity Foundation?

Rosarit was born out of both heartbreak and hope. I witnessed young girls — brilliant, full of potential, forced to abandon education because of poverty, early pregnancies, or abuse. I realized the systems meant to protect them were failing. Rosarit became my answer to that failure: a space where forgotten voices become fierce leaders, where every girl is seen, supported, and equipped for life.

Was there a particular moment or experience that shifted your life’s path toward advocacy and service?

Yes. There was a moment when I sat with a 14-year-old girl who had dropped out of school after becoming pregnant from abuse. Her only question to me was, “Can I still be somebody?” That question wrecked me. It became my rallying cry. From that day on, I promised myself, I would build systems that answer with a resounding, “Yes, you can.”

Winnie Kennedy at the United Nations Headquarters in New York, speaking up for girls’ rights and representing youth-led initiatives on a global stage

Can you tell us about the mission and core focus areas of the Rosarit Girl Child and Humanity Foundation?

Rosarit exists to restore dignity, voice, and opportunity to the marginalized—especially the girl child. Our mission is to break cycles of poverty and powerlessness through education, psychosocial support, leadership training, and economic empowerment. We focus on three pillars: rescuing and rehabilitating vulnerable girls, equipping them with skills and education, and amplifying their voices in community and policy dialogues.

Why did you choose to center your work around the girl child, and how has that shaped your programs?

Because when you empower a girl, you empower a generation. Girls often face the harshest realities; early marriage, abuse, exclusion, yet they carry immense potential. Our programs are shaped by this belief: from safe shelters and mentorship networks to girl-led fellowships and reproductive health education, we design for transformation, not pity.

What makes Rosarit’s approach to empowerment different from other organizations in the same space?

We don’t just serve girls; we co-create with them. Every initiative is informed by their lived realities. Our model combines trauma-informed care with leadership pipelines, ensuring girls move from survival to influence. We also go beyond aid—we foster systemic change by engaging families, schools, governments, and faith institutions in our mission.

What are some of the most impactful projects or initiatives the Humanity Foundation has led so far?

Our “HerPath” program has supported over 500 teenage mothers back into education. Our mobile Clinic outreach units have reached thousands with reproductive health awareness. One of our proudest moments was launching the Girls in Diplomacy Fellowship, where girls from rural and underserved backgrounds now advocate globally on issues affecting them.

How do you measure success when it comes to changing the lives of the girls and communities you serve?

We measure transformation, not just numbers. Yes, numbers are important; we track graduation rates, reintegration stats, and vocational placements. But we also listen for confidence in their voices, leadership in their communities, and boldness in their dreams. Success, for us, looks like a girl who once hid her story now standing on a stage to lead others forward.

Could you share a specific success story that deeply moved you or reinforced your purpose?

Yes, there is one moment that has stayed with me for years and deeply shaped my purpose. I was quite young when I came across something that would forever alter my understanding of injustice and silence. Near a local dumpsite, I noticed a cardboard box. Inside was a newborn baby—lifeless, with a bloated stomach. The child had died, abandoned in the most heartbreaking conditions. We later learned that the baby had been left there by a young girl, likely terrified and alone, who had hidden her pregnancy out of fear and shame.

That moment was devastating. But more than anything, it was a wake-up call. I remember standing there, asking myself: How could a girl go through such trauma, in complete isolation, with no one to turn to? How did we, as a society, fail her so deeply that this became her only option?

That image of a life lost and the invisible girl behind it has never left me. It became the turning point that shaped my path into humanitarian advocacy. I realized that my work had to go beyond awareness campaigns and events. It had to reach the most vulnerable, the most unheard, and it had to create systems of support where there were none.

This experience didn’t just move me—it anchored my mission. That moment broke something in me and built something, too. It became the foundation for Rosarit Girl Child and Humanity Foundation. Every safe space we've built, every girl we've supported back into school, every baby we’ve helped keep safe, has been in response to that day.

One of the most redemptive moments came years later when a 15-year-old in our care, pregnant and rejected, looked at me and said, “If I hadn’t found Rosarit, I don’t know if my baby or I would still be alive.” That, to me, is success—turning silence into safety, and despair into dignity.

It reminded me that behind every issue we seek to address; be it child abandonment, teen pregnancy, or broken education systems, there is often a girl who is unseen and unsupported. My purpose is to find her, to amplify her voice, and to build the systems that make sure she never has to suffer in silence again.

What have been some of the biggest leadership challenges you've faced, and how did you overcome them?

One challenge was leading in spaces where funding was limited but the needs were endless. I overcame it by building strategic partnerships, leveraging storytelling for visibility, and staying radically mission-focused. It taught me how to turn scarcity into creativity—and how to multiply impact without always multiplying resources.

Another major challenge was leading through burnout. I had to learn to rest without quitting, and delegate without guilt. Leadership isn't just about carrying the weight—it's about knowing when to share it.

I've also had to lead through uncertainty—making difficult decisions without all the answers and still being accountable for the outcomes. In those moments, I leaned into purpose, trusted my instincts, and surrounded myself with people who challenge me to grow, not just agree.

Most importantly, I’ve learned to lead with both strength and softness—to hold vision and vulnerability together. Overcoming these challenges wasn’t about being fearless; it was about choosing to show up, again and again, even when it was hard. And that’s what real leadership is to me.

As a female leader in humanitarian work, what unique obstacles have you encountered—and how do you navigate them?

A challenge I’ve often faced is having to prove my credibility in decision-making spaces where I didn’t fit the typical mold of leadership —especially as a young woman in humanitarian leadership. There’s often an unspoken expectation that leadership must look or sound a certain way, and it rarely reflects the diversity of the communities we serve. Navigating that has required me to lead with both confidence and clarity, to let my work speak, but also to speak for myself when needed.

Another challenge has been the emotional labor that often falls disproportionately on women leaders in humanitarian spaces. You're expected to lead with compassion, absorb the trauma of others, and keep going without pause. I’ve had to learn how to set boundaries, prioritize my mental well-being, and model sustainable leadership—not just for myself, but for those I mentor.

There’s also the challenge of balancing urgency with dignity. In humanitarian work, the pressure to deliver quick results can sometimes clash with the need to build deep, community-led solutions. As a woman, I’ve leaned into relational leadership—listening deeply, building trust, and advocating for solutions that center the voices of those directly affected.

I navigate these challenges by staying rooted in purpose, surrounding myself with mentors and allies, Rejecting narrow definitions of what a leader should look or sound like. I’ve learned that I don’t need to lead like a man to be taken seriously—I just need to lead authentically, with vision, courage, and heart.

How do you stay resilient and grounded when the work becomes overwhelming?

I lean into prayer, purpose, and community. I remind myself that I'm a vessel, not the source. When the weight feels heavy, I return to the why—the girls we serve, their stories, their courage. That clarity re-centers me. I also lean on a circle of mentors, friends, and fellow changemakers who remind me that rest is not weakness, and that I don’t have to carry everything alone.

Joy is another key ingredient. I let myself laugh, dance, cry, pause—whatever the moment needs. I’ve learned that sustaining impact means sustaining myself too. So, I create rhythms of rest and reflection, and I make space for grace in the midst of urgency.

At the end of the day, what keeps me going is the quiet conviction that even when the work feels overwhelming, it’s still overwhelmingly worth it.

Winnie Kennedy facilitating a leadership session for girls, equipping them with skills in diplomacy and advocacy

How important is community involvement in your foundation’s efforts, and how do you build trust with local communities?

Essential. We never enter a community as saviors—we come as partners. We conduct listening sessions, involve local leaders in program design, and ensure community ownership at every step. Trust is earned through humility, consistency, and honoring cultural values while challenging harmful norms.

Do you partner with schools, governments, or other non-governmental organizations—and if so, how do those partnerships help scale your work?

Partnerships multiply impact. We work with schools to reintegrate dropouts, with health departments for mobile clinics, and with international NGOs for funding and visibility. Collaboration allows us to scale faster, reach further, and embed our work into systems that last.

How do you ensure that the girls you support are not only educated but also empowered to lead?

We merge education with mentorship, public speaking, entrepreneurship training, and exposure to global platforms. Girls in our programs don’t just learn—they lead peer campaigns, represent us in advocacy forums, and become mentors themselves. We give them space, skills, and a stage.

What is your long-term vision for the Rosarit Foundation in the next 5 to 10 years?

We envision building a global ecosystem for girl empowerment—one that includes leadership academies, a policy think tank led by young women, and a digital hub for girls across Africa and beyond to access mentorship and funding. In 10 years, I want Rosarit to be a recognized force reshaping how the world invests in girls.

If you had unlimited resources, what would be your dream project or initiative?

A “Safe Haven”—a self-sustaining campus that combines a shelter, innovation hub, leadership school, health center, entrepreneurial and agricultural space for at-risk girls. It would be a healing and leadership space where brokenness meets brilliance—and futures are rewritten.

What kind of legacy do you hope to leave behind through your work?

I want to be remembered as someone who disrupted silence, restored voices, and rewrote the future for girls the world forgot. A legacy of courage, compassion, and catalytic change—where entire communities shift because countless girls rise, simply because one woman dared to build something for them.

I hope my life’s work redefines what it means to lead with purpose—that I made impact, not ego, the goal of global engagement; and that I helped make kindness a norm, not an exception, in how we build a better world.

Who inspires you, and what keeps you motivated in this challenging yet rewarding line of work?

Girls themselves inspire me. Their courage to hope—despite hardship—fuels me. I’m also deeply moved by trailblazers, who remind me that young voices can move nations. What keeps me going is the unwavering belief that transformation is possible. Even on the hardest days, I remind myself that every act of service is a seed. I may not live to see the full tree, but I know I’m planting a future where no girl is invisible, voiceless, or forgotten. Purpose is my anchor, hope is my fuel, and the simple truth that purpose is greater than pressure is what keeps me walking forward—no matter how heavy the mission feels.

What advice would you give to young women who aspire to become leaders and changemakers?

My advice to young women is simple: don’t wait to feel ready—step into rooms with the quiet conviction that you belong there, even if your voice shakes. Leadership isn’t about waiting for permission or perfection; it’s about showing up boldly, choosing courage over comfort again and again.

There were moments when I questioned if I was enough—experienced enough, qualified enough, worthy enough. But I’ve come to understand that our stories, our perspectives, and even our struggles are powerful tools for transformation. So, speak up, even when it’s uncomfortable. Take the seat at the table, even if you’re the only one who looks like you. And don’t just walk through open doors—hold them open for others.

Leadership is more than solo acts of heroism; it’s about building communities, coalitions, and movements rooted in empathy, clarity, and purpose. Redefine leadership on your terms, lead with your whole heart, and protect your vision fiercely. The world will try to dim your light or question your worth—but do not internalize those doubts.

You are not just the future; you are the present, and the world desperately needs your voice, your heart, and your leadership now.

Winnie Kennedy visiting local schools as part of outreach efforts, training girls on leadership, civic participation, and global engagement

For our last question, we like to ask our guests to share a moment that was “delightfully chaotic.” The term delightfully chaotic is used to describe a situation or experience that is messy, disorganized, or unpredictable, yet in a way that is still enjoyable and exciting. It implies a positive feeling about the lack of structure and the potential for surprise. Essentially, finding pleasure in the controlled chaos. Please tell us about a moment for you that was “delightfully chaotic” and how that experience shaped you.

In 2019, during our first-ever summit titled “No Ordinary Woman,” we hosted over 300 girls. It was a logistical nightmare—there was a power outage, key vendors didn’t show up, funding was tight, and our keynote speaker canceled at the last minute. Yet, in the midst of the chaos, something extraordinary happened: the girls rose. They led impromptu sessions, danced, recited poems, and stepped in where there were gaps. That day became a turning point for me. I realized the mission was never about flawless execution—it was about creating spaces where girls are empowered to lead, even when nothing goes according to plan. It taught me that when we give girls the space, they won’t just rise—they’ll lead. Even in chaos, they carry the mission forward.

Henna J. Shah is the founder of Delightfully Chaotic and the host of its podcast, Delightfully Chaotic with Henna J. Shah.