Alright – so today we’ve got the honor of introducing you to Jenna Shulman. We think you’ll enjoy our conversation, we’ve shared it below.

Alright, Jenna thanks for taking the time to share your stories and insights with us today. What was the most important lesson/experience you had in a job that has helped you in your professional career?

Early in my career, I was a junior employee at a nonprofit—eager, observant, and still learning how organizations really work. One day, a senior woman in leadership pulled me aside and made it very clear that my role was to stay in the background. Not metaphorically. Literally. The message wasn’t about growth or mentorship; it was about hierarchy and power and knowing my “place.” The way it was delivered stayed with me far longer than she probably ever intended.

At the time, I felt dismissed and belittled. But I absorbed the lesson in a different way than she meant it. I learned exactly how it feels to be made small at work, and how lasting that impact can be. That experience became a quiet but permanent reference point as my career evolved. Every time I moved into leadership, hired staff, or managed someone at an early stage of their career, I remembered that moment—and made a conscious decision to lead differently.

Today, it fundamentally shapes how I treat people. Titles don’t determine value. Entry-level employees, interns, and support staff often see things others miss—and more importantly, they deserve respect simply because they are people. Creating an environment where no one is made to feel invisible isn’t just kind leadership; it’s effective leadership. That early experience taught me that how you treat someone when they have the least power says everything about who you are —and it’s a lesson I carry with me every day.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I began my career on a traditional path—law school with every expectation of entering conventional legal practice. But early on, I realized I was more drawn to a different type of impact than the prestige of law, and I pivoted – into the nonprofit sector. Starting at the ground level, I learned how mission-driven organizations actually function, how relationships are built, and how building trust fuels meaningful work.

Over time, that experience led me to leadership, where I now focus on expanding access, strengthening communities, and building sustainable systems that help people move forward without being burdened by high-interest debt. My work sits at the intersection of strategy, empathy, and execution—bringing people together around shared purpose and tangible outcomes.

Alongside this, I’ve also built a matchmaking venture rooted in the same philosophy: connections matters. Whether in nonprofit leadership or community-building on a smaller scale, I’m proudest of creating spaces where people are seen, supported, and empowered—and of proving that serious impact and warmth don’t have to be mutually exclusive.

Can you tell us the story behind how you met your business partner?

I met my matchmaking partner, Beth, through the nonprofit world—where neither of us was looking to start a business, but both of us were deeply invested in people. She became involved as a volunteer at an organization where I worked, and over time we found ourselves gravitating toward the same conversations: who should meet whom, who might help solve a problem, who would genuinely benefit from being connected.

What started as casual, almost instinctive matchmaking quickly revealed something bigger. We shared a genuine love of connectivity—not networking for the sake of it, but thoughtful, human connection rooted in curiosity and care. We both believed that the right introduction, at the right moment, can change the course of someone’s life.

That shared mindset became the foundation of our matchmaking partnership, which is now almost 12 years old. The business grew naturally out of trust, shared values, and a mutual belief that connection—when done well—is both powerful and personal.

We’d love to hear a story of resilience from your journey.

Early in my career, I was dating someone seriously enough that I met his parents. Over dinner, his father asked about my work. When I explained that I had gone to law school but chose to work in the nonprofit sector, he didn’t hesitate to tell me—quite bluntly—that it was a huge mistake. In his view, nonprofits were places you volunteered your time, not where you built a career. He told me that I had wasted my education.

I remember sitting there, taking in his words, questioning myself in a way I hadn’t before. It would have been easy to let that moment steer me toward the more “acceptable” path. Instead, it clarified something important for me. I realized I didn’t need validation from people who measured success by prestige or income alone. I cared deeply about impact, purpose, and building something meaningful.

That moment didn’t harden me—it strengthened me. It made me more confident in my choices and more resilient when others questioned them. Over time, it also sharpened my commitment to proving that mission-driven work can be serious, strategic, and powerful. Looking back, that uncomfortable dinner became a quiet turning point: I stopped explaining myself and started trusting my own definition of success. And for what it’s worth: I did not marry his son.

Contact Info:

• Website: jelf.org / juluv.com
• Instagram: https://www.instagram.com/jennaleoshul/
• Facebook: https://www.facebook.com/JennaLeoShul/
• Linkedin: https://www.linkedin.com/in/jennaleoshulman/

Image Credits

Jenna Shulman