Built By Educators: A Series on the People Behind Proximity Learning

At Proximity Learning, we believe schools deserve partners who understand their challenges because they’ve lived them. That’s why so many of our leaders — from curriculum developers to executives — are former educators themselves. In this series, we’re highlighting the people who make our mission possible. Each one brings firsthand experience from the classroom, a deep understanding of student needs, and a passion for building something better.

How is Proximity Learning Reimagining the Virtual School Model?

 As education evolves, one thing is becoming increasingly clear: virtual school is not a temporary solution or a second-rate option — it's a powerful, permanent piece of the future of learning. For Kip Pygman, a veteran educator with more than two decades of experience, that reality isn’t just a trend — it’s a calling. His journey from high school teacher to leader at Proximity Learning, a company specializing in live virtual instruction, is a story of conviction, innovation, and heart.

“I’ve been in education for over 20 years,” Kip starts. “I started as a high school business teacher, teaching personal finance, accounting, and digital literacy — and I got involved with online learning pretty early in my career. That’s what really put me on the path to where I am now at Proximity Learning.”

Today, Kip is helping lead the charge to redefine virtual school, not as a backup plan but as a high-quality, student-centered educational option grounded in real-time teaching and relationships.

What does it take to work at Proximity Learning?

Before stepping into the virtual school space, Kip spent most of his career in public education. But his responsibilities quickly expanded. He launched an online credit recovery program for students at risk of not graduating on time, which eventually grew into a district-wide online learning initiative.

His next position provided him the opportunity to conceptualize, launch, and scale an online consortium that spanned three school districts and seven high schools. — the only model of its kind in the state of Illinois and one of very few across the country. Later, he was tapped to oversee online learning for the state of Illinois itself at the Illinois Virtual Schools and Academy

His work in public schools laid the foundation for his future success, but transitioning to the edtech world wasn’t something he took lightly.

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Why He Chose Proximity Learning

“Over the years, I had plenty of opportunities to leave public education and join the edtech space,” Kip says. “But something always felt off. I didn’t feel right in my brain or in my heart making that leap — until I met Evan.”

Evan Erdberg, founder and President of Proximity Learning, offered something different: a mission-aligned organization focused on equity and access through synchronous virtual instruction. “That was the first time the transition felt right,” Kip explains. “It finally felt like a good home — still a part of education, just from the other side.”

What Does Leadership Look Like in a Virtual School Environment?

Since joining Proximity Learning three years ago, Kip has taken on a leadership role overseeing operations and implementation as well as professional development and curriculum design for teachers. His work is grounded in the same philosophy that shaped him in public education.

“One of my mentors always said, in leadership, you have to have more care and concern for the people you serve than for the task at hand,” he shares. “That’s something I carry with me every day. We’re moving a thousand miles an hour here, but the most important thing is always showing care for the people you’re asking to do the work.”

In a virtual school setting, that empathy is critical. Teachers work remotely, sometimes across time zones, but leadership still needs to be present, responsive, and supportive. “Trust and authenticity go a long way,” Kip says. “If you can show that, the results will follow.”

Is Virtual School Better than In-Person?

 Kip is passionate about challenging misconceptions surrounding virtual school. “There’s a tendency to pit face-to-face learning against online learning,” he explains. “One is always seen as better. But that’s a misguided way of thinking.”

Instead, he encourages educators and decision-makers to focus on the true pillars of learning: high-quality teaching, strong curriculum, student support, and effective teacher professional development. “You can have a virtual school class with 15 students and a brick-and-mortar class with 40,” Kip says. “Which one is better? It depends on the teacher, the content, and the support systems. The type of learning modality is just one piece.”

That’s why Proximity Learning prioritizes live, synchronous instruction in its virtual school model. “The real-time interaction with a certified teacher is what makes the difference,” Kip emphasizes.

Facing the Future: AI and Innovation in Virtual Schooling

 When it comes to emerging technologies like AI, Kip sees a clear path forward for virtual schools: embrace it, or risk falling behind.

“Twenty years ago, people were skeptical of online learning. Some thought it would replace teachers,” he remembers. “Whether I agreed with that or not, I saw where things were heading and leaned into it. I think the same is true with AI.”

Kip believes AI will have an even greater impact on students’ lives than adults, and schools — especially virtual schools — need to be proactive. “We have to figure out how to use it to our advantage. If we don’t,  we will all get left behind, including our students, by not preparing them for the world they live in.”

Why Virtual School Teachers Need Support Too

 A key part of Kip’s role is making sure virtual teachers at Proximity Learning receive the support they need. “Teachers are the most direct input into student learning,” he says. “If they’re not supported, that trickles down to student outcomes.”

Professional development, coaching, and curriculum resources are all part of the package. “It’s just as important — maybe more — for virtual school teachers to have those supports,” Kip adds. “They’re working hard to build relationships and deliver results in a digital space, and that requires a unique set of skills and resources.”

What is Proximity Learning’s Mission?

 At the heart of Kip’s work — and Proximity Learning’s — is a deep belief that every student deserves access to a high-quality, certified teacher, no matter where they live or what challenges their school may face.

He references the late educator Rita Pierson, who famously said, “Every child deserves a champion.” For Kip, virtual school can provide that champion when no other option exists.

“Without our teachers, many students wouldn’t have access to the learning environments they deserve,” he says. “That’s the difference we’re making.”

Advice for the Next Generation of Educators

 For new virtual school teachers, Kip offers a simple but powerful message: “Recognize the profound privilege you have in your role. Build strong relationships with your students. When you do, the learning will come more naturally.”

To new employees at Proximity Learning, he offers this: “Be bold. Be brave. Take risks. In a traditional school, innovation can get stuck in red tape. But in our space, you’re free to try, fail, try again, and that’s encouraged here.”

Leading the Future of Virtual Schooling

 Kip Pygman’s career reflects a changing educational landscape, one where virtual school isn’t just a contingency, but a cornerstone of equity, innovation, and opportunity. With leaders like Kip at the helm, and organizations like Proximity Learning committed to student success, the future of virtual education looks brighter than ever.

And behind it all? A simple truth that Kip has never lost sight of: Every student counts.

Check out our other former educators from Proximity Learning.