Spring | 2026
Clear is Kind
"How can I make these kids feel valued, feel seen, feel heard during some of the hardest years of their lives?"

Cassie Jennings wasn't looking for a new job. She had spent a decade at the alternative school in Chana — serving students who had been expelled or suspended from their home districts across Ogle County — and she loved the work. Then a teacher in the Byron district reached out and told her about an opening for an assistant principal at the high school. She hadn't heard about it. She applied anyway. "This is what I would want to do," she says. "I love high school. I love that assistant principal role where you work with kids on behaviors. That's what I've always done."
That was this school year. She's in her first year, and she's already changed how the building handles the space between small problems and big ones.
Cassie grew up in Stillman Valley — a rival of Byron's, as she notes — graduated from Trinity International University in Deerfield, where she played basketball, and earned two master's degrees: one in curriculum and instruction, one in educational leadership. She started her career in Rockford at an alternative school, then spent a decade at Chana, the Ogle County alternative placement school, where she taught PE and later served as a behavior interventionist — coordinating intake and exit processes for students in the Safe Schools program. A decade with kids navigating the hardest circumstances turned out to be excellent preparation for the job she has now.
At Byron High School, with roughly 465 students, she has built a new referral framework that keeps teachers and administrators connected before problems escalate. When a teacher has a conversation with a student about something going wrong in class, they log it. That way, when a formal referral eventually comes in, Cassie can approach the student not as a stranger delivering a consequence, but as someone who already knows the backstory. "I can say, 'I know this teacher already talked to you about it — this is a second conversation we're having, not a first,'" she explains. The goal is to keep small things small. In a building where she describes the students as "truly fantastic," that often means the small thing stays small and never becomes anything more.
Her philosophy about clarity shapes how she approaches everything. "Clear is kind," she says — a phrase she returns to more than once. Kids want to know exactly what's expected of them and exactly what happens when those expectations aren't met. Remove the ambiguity, and most students will meet you where you've drawn the line. Leave the gray area, and you invite confusion that can look like defiance but usually isn't.
What may be most distinctive about her approach is what she does when nobody is in trouble. She stands at the door every morning to greet students by name — still learning all 465 of them, but working at it. She walks through the building, parks a cart in the hallway, and works from it so she's visible. She rotates through lunch tables, sits with different groups, just talks. She goes to extracurricular events. Some students have started coming into her office voluntarily — not because they're in trouble, but because they know her and her room is a comfortable place to read before class. "I really feel like you should be invested in your kids more than just sitting in the office and calling a kid in when they're in trouble," she says.
She also makes positive phone calls home — intentionally, consistently, targeting the students who never get sent to her office but deserve to be seen. "It's not just the kids in trouble that I'm talking to," she says. "I see your kid making great choices." For parents, hearing that unprompted is its own kind of culture shift.
Ask her what success looks like three years from now, and she answers without hesitation. "Kids are smiling when they come in. Every kid feels seen, and every kid feels cared for." She knows that's harder than it sounds. "Making sure every kid feels seen — that can be really hard." She's trying to do it anyway, one lunch table at a time.
Cassie lives in Stillman Valley with her husband, a farmer, and their nine-year-old twin daughters, Ava and Joanna, who attend school in the Byron district. She grew up on a farm, was active in FFA and 4-H, and fully expects her daughters to follow that path. When the girls were in kindergarten, they brought a baby calf to school for show and tell. Some things are just in the family.
"My goal is always to be the adult I would want for my own kid," she says. "How can I make these kids feel valued, feel seen, feel heard during some of the hardest years of their lives?" It's a question she shows up and answers every day. Byron is lucky she picked up the phone.
