Highlander Excerpt: Q&A with Jessica Deller-Hubbard, Executive Director of Breakthrough San Juan Capistrano

At a time of continued growth and opportunity for Breakthrough San Juan Capistrano, the organization welcomed Jessica Deller-Hubbard, M.S., J.D., as the new Executive Director whose leadership is grounded in experience, purpose, and a deep belief in the transformative power of education. A respected education and nonprofit leader, Mrs. Deller-Hubbard brings a thoughtful, student-centered approach shaped by years in classrooms, strategic leadership, and community-based work.

Breakthrough SJC stands as a model of what sustained access and high expectations can achieve, serving more than 250 students traditionally underrepresented in higher education across middle school, high school, and college pathways. Mrs. Deller-Hubbard describes the mission as both deeply personal and aspirational, reflecting a career devoted to opening doors and cultivating possibility. As Breakthrough SJC continues to grow, the focus remains on expanding opportunity with intention, and building a lasting community where students are supported to succeed.

When I stepped into the role of Executive Director at Breakthrough San Juan Capistrano, the mission immediately felt familiar to me. Joining the St. Margaret’s team has, in many ways, felt like coming home, because the work and values of this school reflect a belief I have carried for a long time: that education is the great equalizer. It has the power to change circumstances, open doors that once seemed sealed shut, and allow young people to author futures that might otherwise feel out of reach.

When I first learned about Breakthrough SJC, it felt like the mission of my heart and many of my long-held convictions about education were made real. The things I have believed, lived myself, advocated for, and frankly talked about at dinner tables for years were already being practiced here, thoughtfully and with intention. I knew this was a moment when programs like Breakthrough are not just impactful, but essential. That responsibility mattered to me, and it inspired me in the way all meaningful challenges do.

My first priority as a leader was simple and very deliberate: to learn. As a former middle school teacher and a lifelong student, can you expect anything else? That felt like the only responsible place to begin. I wanted to learn from my brilliant Breakthrough and St. Margaret’s colleagues, from the families we serve, and most importantly, from our students. We have the incredible privilege of having two Breakthrough alumni on our team who chose to return to Breakthrough and serve the very community that helped shape them. That kind of full-circle commitment speaks volumes about the strength and integrity of this work and its mission.

I wanted to begin by better understanding the magic that was already here so I could protect it, strengthen it, and help it grow. Leading Breakthrough SJC has been about honoring what makes this program special while ensuring it continues to expand opportunity for generations of students to come.

My career across education, nonprofit leadership, and strategic consulting has shaped how I think about impact in a very integrated way.

At my core, I am an educator. That grounding keeps students at the center of every decision and reminds me that impact is deeply human. It shows up in classrooms, in relationships, and in the steady, long-term support that allows young people to imagine and pursue bigger futures for themselves. I want that for every student I have ever met, and every student I have yet to meet.

My legal training informs how I think strategically. Law teaches you to gather all available facts, understand context, anticipate risk, and build a clear, defensible plan. That discipline translates directly to leadership. It encourages thoughtful decision-making, careful stewardship, and clarity about what matters most. 

Underlying all of this is a nonprofit philosophy rooted in abundance. I realize that may sound wildly counterintuitive in education and nonprofit spaces, where scarcity often dominates thinking. I understand where that insecurity comes from, but I do not believe you can expand opportunity by operating from a mindset of limitation. You cannot build abundance with scarcity. You can only build it by believing it is possible and committing thoughtfully to creating the conditions for it. Only abundance will build abundance. That is abundance in giving and abundance in imagining what is possible.

I learned this lesson about abundance long before I ever led an organization. I was a middle school teacher at a Title I school in central Florida, and I carried the very real responsibility of improving my students’ state testing scores. The stakes were high. Many of my sixth graders were reading below grade level, and the school needed those scores to improve in order to maintain its grade and funding.

The safer choice would have been to narrow the curriculum, simplify the texts, and focus only on remediation. Instead, I chose to take a calculated risk. I decided to teach Shakespeare. Julius Caesar.

It raised eyebrows. But Caesar is a story about betrayal, cliques, power, and groupthink. Honestly, there are few texts better suited to middle school students. I believed my students could handle more than we were giving them credit for, and I was willing to take the risk to prove it. They didn’t just follow the story, they engaged with it. They debated it. They understood it.

That year, their reading scores showed some of the largest gains the school had seen in years. Abundance built by abundant thinking and believing. I taught Julius Caesar every year after that.

For me, expanding Breakthrough’s impact means leading from a belief in what is possible for students, even when that belief feels ambitious. I believe every Breakthrough student is worthy of extraordinary opportunity, not because of where they start, but because of what becomes possible when they are challenged and supported.

That belief comes from experience. I have seen how expectations shape outcomes, and how quickly opportunity expands when students are given permission to see themselves differently. It informs how I work and how I make decisions, especially when it comes to strengthening what already works and growing Breakthrough in ways that are both bold and responsible over time.

Success, to me, looks like Breakthrough growing in reach and influence while remaining deeply rooted in community and the secret recipe that built this program to begin with. I want more students across Orange County to have access to this experience, because it works, and because it is necessary.

But growth is not just about numbers. It is about identity and belonging. One of my aspirations for Breakthrough is that it becomes a lifelong community for students, alumni, families, mentors, and supporters. St. Margaret’s does this beautifully. There is a shared understanding that when you encounter someone shaped by this community, it signals something meaningful. Shared values. Shared standards. A commitment to lifting one another up. I want Breakthrough to offer that same sense of belonging and continuity for the students we serve.

I also want the Breakthrough experience to open doors well beyond the classroom, just like St. Margaret’s. To education, yes, but also to mentorship, networks, careers, and opportunity. I want our students to walk into any room, academic or professional, with the same confidence and sense of belonging as any other student, knowing they can contribute, compete, and lead.

Deepening Breakthrough’s role in the community means inviting others into that vision. Families, schools, alumni, and supporters who believe in investing in young people and in each other. When Breakthrough is at its best, it is not just a program students participate in. It is a community that stands with them for the long term, and that is the kind of growth I am most excited to build.

I come from a background that was challenged by poverty, raised in a multigenerational Cuban-American home where resources were limited but expectations were high. From a young age, I believed, and still believe, that higher education is the greatest power we have in this country. I believe that because I have lived what it can do.

By many measures, the data says I should not be here. And yet I am. Not because of luck, but because education opened doors that completely rewrote my future. Those letters after my name represent access, opportunity, and agency. They changed what was possible for me.

That experience shaped my belief in educational equity. I do not believe in this mission because it sounds beautiful, though it is. Or because it is abstractly inspirational, though it can be. I believe in it because I have seen, firsthand, how education can change circumstances, expand options, and invite people into rooms they were never expected to enter. I believe in this mission because I have lived its impact.

Wanting more students to be invited to the table is not an abstract idea to me. It is personal. It is practical. And it is grounded in the knowledge that when students are given access, support, and high expectations, they do not just rise to the occasion. They redefine what is possible.

Teaching middle school shaped everything about how I connect with students and families, because it taught me how to meet people where they are without letting circumstance define what comes next. Middle school is a time of uncertainty, self-doubt, and enormous potential. It is also no accident that Breakthrough’s work begins in seventh grade. That is often the moment when students begin to internalize beliefs about who they are, what they are capable of, and where they belong.

Oftentimes, the greatest gift you can give a student is a dream they cannot yet dare to imagine for themselves. I experienced that firsthand. When I was in sixth grade, a teacher believed in me enough to stretch me, challenge me, and offer me a vision of what might be possible before I could see it myself. That belief changed my trajectory. It led me to the right high school, then to a full scholarship for college, and ultimately to opportunities that reshaped my life.

That is the posture I bring to my work at Breakthrough. Connecting with students and families means acknowledging how daunting this path can feel, especially when no one in your family has ever done this before. It means saying, with clarity and care and certainty, that higher education is not only possible, it is a place where they belong.

Advocacy, for me, is about holding that belief on behalf of students until they are ready to hold it themselves. And when that happens, the impact extends far beyond one student. It changes families, communities, and generations to come.