When Terry Tippett first walked into the School District of Lancaster in 2005, the district’s technological landscape looked vastly different. There was no Wi-Fi. No iPads. No mobile flexibility. Desktops were hardwired to walls, email couldn’t be checked on the go, and if you wanted to capture meeting notes, you had to bring a pen.
In those early days, what Terry saw wasn’t a problem, it was potential. Two decades later, as she prepares to retire as the Director of Technology, that potential has grown into a thriving, tech-enabled ecosystem, built through years of quiet resolve, hard-earned expertise, and a leadership style rooted in compassion, clarity, and community.
From Curiosity to Career
Terry didn’t originally set out to become a leader in technology. In fact, she once considered becoming a paralegal. She wanted to help build cases behind the scenes, less interested in the spotlight and more drawn to the details that shape outcomes. That same behind-the-scenes dedication would eventually define her work in education. After dabbling in coursework and entering the workforce, Terry discovered a curiosity about how computers worked, and what made these “little boxes” tick. She learned by doing, taught herself through trial and error, and took courses that sharpened her skills.
Eventually, her interest in technology intersected with a career in education. Terry began supporting student information systems in Maryland’s county-based school system, larger and more complex than what she would find in Lancaster. When the opportunity arose to apply at SDoL, she was hesitant at first. She wasn’t selected the first time she applied, but a nudge from then-assistant superintendent Matt Stem encouraged her to try again. She did, and that second chance changed the course of her career.
A Foot in the Door and a Seat at the Table
Terry began as the SIS (Student Information Systems) Coordinator. Over the years, she found herself stepping in as interim director again and again, often during leadership transitions. Eventually, then-superintendent Pedro Rivera sat her down. With his support and a shared belief in open, honest communication, Terry finally accepted the official role of Director of Technology.
From that point on, she helped shape the future of the district’s digital infrastructure, not just as a technical leader, but as a mentor, collaborator, and relentless advocate for what technology could do when used to empower. But she never did it alone. “This team is so amazing,” she often says. “They make my life purposeful and easy. Without them, I’m nothing.” Terry has always led with this mindset that her success is shared, and her role is to support the people doing the work.
Transforming the District Through One-to-One Access
Under her guidance, the technology department evolved into a multi-faceted operation that includes infrastructure, mobile device management, AV support, help desk services, programming, and student information systems. Every time a screen lights up, a digital form is submitted, or an iPad is repaired and placed back in a student’s hands, that’s her team in motion.
Among her proudest achievements is the implementation and expansion of the district’s 1:1 initiative. It didn’t happen overnight. “When we started,” Terry recalls, “I asked teachers what 1:1 would look like. And they said, ‘You tell us.’” That initial hesitation was the beginning of an ongoing dialogue, one that would take years of planning, cross-department collaboration, and strategic budgeting to bring to life. But today, every student in the district has access to a personal iPad, thanks to a thoughtfully built infrastructure and a sustainable refresh cycle that Terry championed.
That investment paid off during one of the district’s most challenging periods: the COVID-19 pandemic. While many were able to work from home, Terry and her team showed up in person, day after day. They gathered devices from every building, sanitized them, packaged them, and distributed them to families in parking lots, rain or shine. “We lived through all four seasons in one week,” she jokes. But there was nothing lighthearted about the responsibility they carried. “We were scared,” she admits, “but we knew what had to be done.” Her leadership during that time was steady, solution-oriented, and deeply grounded in care for the community.
Terry’s approach to leadership isn’t about having all the answers, it’s about asking the right questions. It’s about listening, especially when it’s hard. And it’s about being honest, even when the answer is no. “I used to be the no person,” she says. “Now, I say, ‘Let’s talk through it. Here are some options.’” That shift in perspective didn’t just change how decisions were made, it changed how people around her felt empowered to speak, share ideas, and innovate.
Mentorship and making space for others
That open-door attitude has led to a ripple effect of success stories. Several women who once served as her administrative assistants, have moved on to thrive in new roles across the district and beyond. Each departure was bittersweet, but Terry cheered them on. “Don’t stay just to stay,” she tells them. “Go for it. You can always make a change later.” Her ability to spot potential, nurture growth, and support others in their journey has made her not just a manager, but a mentor.
Even in her final year, she continues to reflect on how the department can better meet students where they are. From re-evaluating which devices best serve high school learners to holding space for conversations about student behavior and digital responsibility, Terry doesn’t shy away from complexity. “It’s not one-size-fits-all,” she says. “We have to listen to what students need, not just what we think they need.”
More than just tech
That empathy extends to the small but powerful traditions she’s fostered like the annual teddy bear holiday celebration with students from the Multi-Disabilities Support Program. Terry began the tradition years ago, personally purchasing stuffed animals to give to students as they sang carols and visited the department. Over time, her entire team joined in, each member holding a bear to pass along to a child. “These kids touch my heart,” she says. “And I want them to know we’re here, we see them, and we care.”
Looking ahead, with gratitude
As she prepares for her next chapter, one filled with grandkids, travel, and perhaps a new way to make a difference, Terry leaves behind a district that is not only more connected through technology, but also more connected to one another. When asked what legacy she hopes to leave, her answer is characteristically simple, yet rich in meaning: “That I was here. That I was present. That I cared.”
That care is evident in every system built, every team member mentored, every student supported, and every thoughtful decision made with the district’s best interest in mind. And though Terry may be stepping away from her office, her impact will continue to run quietly behind the walls, just like the networks she helped build.
