Leading with Kindness: Debbie Cavalier’s Vision for the Future of Music Education

Debbie Cavalier has spent her career expanding access to music education and adapting to the ever-changing landscape of technology. As the CEO and co-founder of Berklee Online, her leadership has helped the college grow into the world’s largest online music school, providing opportunities for students around the globe. This year she is being recognized with the Julius M. Nolte Award for Extraordinary Leadership from UPCEA, an organization that has had a profound synergy with Berklee Online over the years.

But what makes Cavalier truly deserving of such a rare award isn’t just what she’s done—it’s also how she’s done it. In a world where leadership is often associated with authority and tough decision-making, Cavalier has built a legacy on something rarer: fostering an environment of kindness and support to lead to innovation.

In the letters nominating Cavalier for the Nolte Award—UPCEA’s most prestigious honor, given for “unusual and extraordinary contributions to the cause of continuing education”—nearly every person mentioned one defining quality: kindness.

Michael Moyes, Berklee Online’s COO, describes her as “caring, kindhearted, and considerate,” adding that he has “been a beneficiary of her thoughtful and calming approach” for 16 years. Jessie Cappuccilli, Berklee Online’s Executive Assistant and Project Manager, says, “she has developed such a special community that we’ve had several staff members leave to pursue other jobs, only to return months or years later!”

According to Cavalier, it was her uncle, Sandy Feldstein, who taught her that true leadership isn’t about power—it’s about people. Feldstein was a renowned music educator and publisher who helped shape the landscape of educational music materials used by teachers and students across the country. At the helm of Warner Brothers Publications, a $40 million company, he managed a staff of 300—including Cavalier herself.

“His whole approach was nothing but authentic kindness,” she says, remembering his mentorship. “People loved him and went the extra mile. And it was just this really wonderful culture that everyone loved being part of.”

That lesson stuck. From her early days as a music educator to her rise as an executive, Cavalier carried that same philosophy forward. 

“Without naming names, I’ve had the absolute opposite experience of that as well, and it became clear to me that whatever your role, whether it’s leading an organization, leading a team, or just interacting with peers, it makes no sense to be anything but your authentic self,” she says. “Thankfully, for me, the kindness piece does feel authentic.”

In her acceptance speech at the UPCEA awards event, Cavalier dedicated this award to Roger H. Brown, Berklee’s third president. “Roger recognized something in me and entrusted me with the leadership of Berklee Online after a decade as the founding academic dean. At the time, I was an untested CEO, but Roger gave me the opportunity to lead and mentored me week after week during that crucial first year. This experience taught me a powerful leadership lesson: sometimes, a spark of belief in someone means more than experience itself. It’s a lesson I carry forward in my own leadership and I will always be grateful to Roger.”

Debbie Cavalier and her team have created the most innovative and comprehensive online music education program in the world. I’m so proud of her work and her leadership.

— Roger H. Brown, former president of Berklee College of Music

Cavalier’s approach to leadership has also left a lasting impression on students—not just as an administrator but as a teacher. In addition to serving as CEO, Cavalier continues to teach Music Theory 101 at Berklee Online, a rarity among leaders at her level. Kamilah Marshall, a backing vocalist for Taylor Swift and Berklee Online alum, recalls the impact Cavalier had on her in the virtual classroom. 

“Debbie was my very first music teacher during my first semester at Berklee, and from the moment I started her class, I knew I was in the right place,” she says. “She was not only kind and patient, but her teaching style made a lasting impact on me as a student. Her approach to teaching theory was both efficient and inspiring, and she created an environment where learning felt engaging. Having her as my first instructor was an awesome way to begin my journey at Berklee.”

Pioneering Innovation at Berklee Online

But all of this kindness on its own probably wouldn’t have merited an award so rare that it’s not even given out every year. Throughout her tenure at Berklee Online, Cavalier has been at the forefront of several major milestones that have expanded the reach of music education. Under her leadership, Berklee Online launched its first online degree programs, making Berklee’s renowned curriculum accessible to students at a fraction of the cost of on-campus tuition. 

As Brown wrote in his nominating letter to UPCEA, because of Debbie, “students join from all over the world, including countries from which US visas would be next to impossible to attain.”

Cavalier also played a key role in Berklee Online’s early adoption of courses through platforms like Coursera and edX, helping millions of students engage with music education on a global scale. She also spearheaded partnerships with organizations such as the US military and developed pathways for former Berklee students to complete their degrees online. 

Embracing Technology, Thoughtfully

Cavalier’s ability to spot opportunity in emerging technology has deep roots. As a student at Berklee in the 1980s, she was already experimenting with MIDI files and synthesizers—tools that were still new to the classroom and stage. Later, while working in music publishing, she helped develop some of the first educational materials to incorporate digital tools like MIDI accompaniments and interactive CD-ROMs.

“Technology and music education was just this thread for me,” she says.

These early experiences laid the groundwork for her role in shaping Berklee Online into what it is today: a program that meets students where they are, both geographically and technologically. Her passion for education also took a creative turn through Debbie and Friends, a Grammy-winning children’s music project that allowed her to blend teaching, songwriting, and performance. 

“When you’re writing songs for children, there has to be something meaningful for them to do in that song, to make it an engaging experience,” she says.

Today, Cavalier continues to guide Berklee Online’s approach to emerging technologies like AI and virtual reality. Under her leadership, the college is piloting AI tools that identify at-risk students earlier than traditional metrics would allow, and has launched BOB (Berklee Online Bot), an in-house AI tutor that supports students with their coursework, using the Socratic method—prompting critical thinking rather than handing out easy answers.

These efforts align with Berklee Online’s expanding curriculum around music and AI, including new courses such as AI for Songwriters and AI for Music and Audio.

“We really need to make sure that our students are well informed and well equipped to make the decisions of how to use or not use what’s available to them, and not be blind to it,” she says.

A Lasting Impact

UPCEA has been an invaluable partner to Berklee Online throughout our journey. In our early days, they were my go-to resource for connecting with other online administrators and finding essential support. When online learning was still emerging, their conferences consistently featured dedicated tracks on the subject. Once we established ourselves, UPCEA was the first organization to recognize Berklee Online’s commitment to quality and innovation. Over the years, they’ve honored our courses, instructors, and students with numerous awards. That history with UPCEA makes this special award from them particularly meaningful.

— Debbie Cavalier

Cavalier’s contributions have had a ripple effect not only within Berklee but across the field of online education. Robert Hansen, CEO of UPCEA, recalls the moment he fully understood the scope of her influence: “Debbie told a stunned audience that what she had just shared with them was about to be replaced by a next-gen version. For most of us in the room, even the ‘dated’ version was a privileged glimpse into the future. The promise of online education seemed limitless that day.”

Brown echoes that sentiment, emphasizing Cavalier’s unique vision and staying power. 

“Debbie is an uncommon leader,” he says. “She is a thoughtful, deliberate, caring person who had an early vision for what online learning might become at Berklee and has steadfastly seen her dreams come true and has helped Berklee expand its reputation and reach dramatically.”

He also points to her ability to unite others around that vision. “Debbie’s first heavy lift was convincing faculty to help develop online courses. Having been an alumna of the school and bringing both musical credibility and knowledge of the Berklee culture, she recruited several of the most widely admired faculty to develop the initial courses. … Within a few years, the widespread skepticism of the faculty had turned into a waiting list of people hoping to develop new courses.”

As she receives the Nolte Award, Cavalier remains focused on the work ahead. 

“I don’t want this piece to be all about me,” she says during the interview for this article. “But rather the work we do.”

Yet without her leadership, that work—and the impact it continues to have—might never have been possible.