New Directors Focus on Educational Equity

Chelsea Penney
December 17, 2021

The Proximity Learning team is expanding! We are thrilled to welcome new employees and new departments to our growing company. As we evolve, we have recognized new needs that can be fulfilled by experts like Daryl Chesley and Kip Pygman. Learn more about our new leaders!

Daryl Chesley, Director of Innovation

Proximity Learning is thrilled to welcome Daryl Chesley to the team! Our new Director of Innovation is primed to pioneer this role because he has worked in mission-driven, service organizations for his whole career. First, Daryl worked in the US Navy while completing his Master's in Education. Then, he taught for several years before becoming a high school principal and continued to work as an administrator at the district level. From there, Daryl joined the United Network for Organ Sharing, where he established the education program for the nonprofit. 

Daryl enjoys being active every day and recently summited Mount Washington in New Hampshire! He is excited to join Proximity Learning, where achieving the mission is the clear focus of all operations. "I have been in plenty of places where you don't remember the mission statement because it's so long and confusing." He feels differently about Proximity Learning's clear mission, 'Connect all learners with the expert teachers they deserve.' "And what's really compelling there is we're not displacing any teachers. The alternative is that kid doesn't have a teacher. The power of that forms around that fact. We're impacting students, families, communities. That's something that keeps you focused. At Proximity, we are tackling that equity in education issue."

What is Daryl looking forward to?

Daryl is excited to bring his experience in educational leadership and process development to the department. As the Director of Innovation, he will oversee three pillars: curriculum, professional development, and innovation. "My job is all about supporting teachers." Daryl is laser-focused on helping teachers with top-tier curriculum, continually updated professional development, and rich resources. In addition, he will identify future, innovative resources to be at the forefront of education technology.

"We are making a difference. The alternative for these students is that they don't have a teacher. We are providing that high-quality teacher. That's very powerful every day, especially in those rural and urban areas that are completely understaffed and overwhelmed. That's how you change communities by changing access to education."

"As Proximity Learning grows, that means we're having a bigger impact on students and communities."

Daryl with wife, Kate, at the summit of Mount Washington

Kip Pygman, Director of Virtual Schools

Welcome to Proximity Learning, Kip Pygman! Our new Director of Virtual Schools spent his whole career in public education as a teacher, administrator, and virtual education director. He built or led online learning programs at the school, district, multi-district, and most recently the state level across Illinois before joining our national organization. He has created virtual education programs from scratch and pioneered roles, so he is well-suited to develop this branch of Proximity Learning.

Proximity Learning’s core values and mission were critical for Kip to transition from public education to a private edtech company. He matches the core values of integrity, innovation, and passion to his priorities and feels empowered to achieve the mission of connecting all learners with the expert teachers they deserve. In addition, he is driven to provide educational equity to students around the country. 

What are Kip’s goals?

“I will make sure on the virtual side that when somebody partners with us, they are getting the quality educational experience that they expect and that we expect. So doing my part to ensure that happens. Equipping and empowering our teachers to move from their point A to their point B, even if that’s different from teacher to teacher and making sure that they have the tools and the resources to do what they do best and teach.”

Kip is looking forward to learning about virtual education nationwide and distinguishing the differences between state requirements. In addition, he is excited to experience the diversity in state needs and goals when it comes to remote instruction.

“I’m looking forward to working alongside other thought leaders and teams members that share in the same passion, to gather so many amazing and talented people who are all working toward the same goal and have the same passion. It’s a pretty neat environment to be part of. I’m also looking forward to the challenge. Building a virtual school is complex and very nuanced. It’s complex internally; it’s also complex externally because there’s still a lot of perceptions by people in the educational field that online learning is inferior to face-to-face learning, so that brings its own set of inherent challenges as well. But I enjoy the challenge, and I embrace it.”

Educational Equity

“A lot of people talk about equity,” Kip says. “It’s an easy thing for people to just talk about, but not as many people put in the work and the effort into action to address equity. I’m very excited to be a part of the solution and not just talk about it. When we talk about equity, it’s often misguided like you saw during the pandemic. ‘Well, let’s just get a device into the hands of everybody. Let’s get the internet into the hands of everybody. Everything’s going to be okay.’ Although that’s important and kids certainly needed the device, they needed the internet, but they also needed a teacher. And they need a quality teacher, so there’s a lot more to it than just a device and internet for that equity piece. It’s also providing a high-quality teacher, a high-quality curriculum. Proximity Learning is doing its part to address that equity piece as a whole, so I’m very excited to be a part of that.”

“A good teacher doesn’t need much inspiration. Inspiration runs through their veins like blood; that’s why they went into teaching. They didn’t go into it for the glory, the accolades, the money. They went into it to serve. So recognizing that to me is to equip them and empower them to do what they do best. What is it that they need to be successful in their virtual classroom environment? Beyond that, to have more care and concern for them as people that way they’ll feel like they’re part of a community and they’re cared about and that their work is appreciated and valued.”

Kip and fiance Christine at the Palmer House Hotel in Chicago, IL

Welcome Daryl and Kip!

Learn more about our careers here.


Chelsea Penney earned her Bachelors Degree in Writing from University of Colorado Denver. She is currently in graduate school through Texas A&M University studying Marketing. She loves living in Austin, TX and working on the frontline of the many marketing initiatives for Proximity Learning.

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