Last year, the AB50C Awards honored 50 exceptional leaders. But who are they beyond their roles? We spoke with these leaders to uncover the stories, passions, and perspectives that shape them and what truly sets them apart.

Why He's a Champion

Kevin Fleming has spent more than two decades helping institutions build stronger connections with the people who matter most.

As co-founder and CEO of Prosper Nonprofit Advisors, he has built a career around bringing people together, whether that's helping alumni reconnect with their alma mater, guiding institutions through strategic change, or supporting advancement leaders as they tackle complex challenges.

His work sits at the intersection of strategy and human connection. Through consulting, research, and thought leadership, Kevin continues to shape how institutions engage, understand, and inspire their communities.

It's a commitment that earned him recognition as an AB50C champion and the title of The Unifier.

Beyond the Title

When Kevin learnt he had been named an AB50C champion, his first reaction was simple: surprise.

Then came excitement.

He immediately shared the news with his family and found himself reflecting on the company he was joining. Being recognized alongside so many respected peers in advancement felt both humbling and meaningful.

"I was really surprised. I was very, very excited."

The recognition resonated because it aligned so closely with the work that has defined his career.

For Kevin, advancement has never been just about campaigns or engagement metrics. It's about helping people feel connected to their institution, to one another, and to a larger story.

That belief shows up in the way he works with clients today. In fact, many jokingly refer to him as their "advancement therapist".

Behind the joke is something deeper: Kevin genuinely enjoys being a thought partner, helping leaders navigate challenges and reminding them they don't have to do it alone.

What Winning AB50C Meant to Him

The title of The Unifier felt especially fitting.

Throughout his career, Kevin has focused on bringing people together and ensuring every voice feels valued and represented.

Whether working with alumni, volunteers, or advancement teams, his goal has remained the same: create spaces where people feel connected and invested in the future of an institution.

"My charge has always been to bring people together."

For Kevin, the award wasn't simply recognition for what he's accomplished. It was recognition for the values that have guided him throughout his career.

Finding His Way into Advancement

Kevin didn't set out to build a career in advancement. His journey began as a student tour guide at James Madison University. After graduation, he took a role in admissions before an opportunity at the University of Connecticut Alumni Association introduced him to alumni engagement.

It felt like a natural fit. His own college experience had been transformative, and helping alumni maintain that connection resonated deeply with him. Like many advancement professionals, his path wasn't linear.

At one point, he left alumni relations to pursue a master's degree in student affairs because he missed working with students. While he loved that experience, he eventually realized alumni relations offered something unique: the chance to work across an entire campus community.

Over the years, he continued to follow opportunities that challenged him to grow.

He spent years commuting long distances away from family to advance his career. He pursued advanced degrees he never originally planned to earn. Eventually, he started a business he never imagined himself owning.

Each chapter reinforced a lesson that continues to guide him today:

"Be willing to surprise yourself."

The Work That Matters

Today, Kevin serves as Co-Founder and CEO of Prosper Nonprofit Advisors, a consultancy specializing in strategic planning, fundraising, board engagement, and alumni engagement.

No two days look exactly alike. One day he might be helping a university prepare for a major campaign. Next, he could be facilitating strategic planning sessions or helping nonprofit leaders work through organizational challenges.

What excites him most isn't necessarily the variety of projects; it's the opportunity to work with good people.

Many advancement leaders are expected to have all the answers while carrying significant responsibilities. Kevin enjoys creating space for those leaders to think, reflect, and grow.

"My favorite part is making people feel like they have an advocate and opportunity for peaceful reflection."

Looking ahead, he's focused on growing Prosper and expanding its reach. He's also exploring a new venture centered around alumni survey research, inspired by his doctoral work examining the connection between graduate student experiences and alumni giving.

For Kevin, understanding alumni sentiment – how people feel about an institution – remains one of the profession's greatest opportunities.

An Initiative He's Proud Of

Among the many projects Kevin has worked on, one stands out.

His team partnered with the University of Hartford as it navigated a historic transition from Division I to Division III athletics.

The project required balancing NCAA requirements with broader considerations around student life, recreation, wellness, and community engagement. Together, they developed a comprehensive five-year strategic plan to guide the transition.

What made the work particularly meaningful was its uniqueness. To Kevin's knowledge, it was one of the first strategic plans developed specifically for a transition of this kind.

He's equally proud of Prosper's work helping Holyoke Community College prepare for a transformational gift and supporting Morgan State University's campaign readiness efforts.

Across every engagement, the goal remains the same: helping good organizations do good work more effectively.

A Thoughtful Approach to AI

Kevin sees AI as a powerful addition to the advancement toolkit.

Used well, it can reduce repetitive work, speed up processes, and help professionals refine their thinking. But he believes there's an important distinction between assistance and replacement.

For Kevin, advancement remains fundamentally human.

The profession is built on relationships, empathy, trust, and connection. While AI can support that work, it can't replace the conversations and relationships at its core.

"The heart of what we do is human thought, human emotion, and human connection."

Rapid Fire

Where It All Comes Together

If there's one theme that runs through Kevin Fleming's career, it's connection.

In a profession increasingly focused on engagement, belonging, and impact, Kevin's story serves as a reminder that advancement is ultimately about people.

The tools may change. The technology may evolve. But meaningful relationships remain at the centre of everything. That's what makes Kevin a true Unifier and why his story embodies the spirit of Humans of Advancement.