Her Story
About Jennifer
Jennifer Chestnut is the Principal of Pendleton Heights Middle School in Pendleton, Indiana, a position she has held since June 2019. Her career in education spans nearly four decades, beginning as an elementary music teacher in Bloomington, Indiana, and continuing through roles as a middle and high school teacher, athletic director, and assistant principal within South Madison Community Schools before she stepped into the principal role. Across her career, she has guided instruction, operations, school culture, and crisis preparedness, and has led the planning and opening of new school facilities while overseeing the hiring, supervision, and evaluation of staff. Chestnut's academic preparation reflects the breadth of her professional path. She holds a Bachelor of Science in Music from Indiana Wesleyan University and a Master of Science in Secondary Education from the University of Southern Indiana, along with administrative leadership coursework from Ball State University and special education coursework in mild-to-intense interventions from Taylor University. She holds active Professional Educators Licenses in both Mild and Intense Intervention through the Indiana Department of Education, and her broader expertise extends into high-ability programming, school safety planning, and mentorship of new administrators and student teachers. She is an active member of the Indiana Association of School Principals, the National Association of School Principals, the National Association of Middle School Principals, and ASCD. Chestnut's contributions to education have been recognized with a Distinguished Service Award from the Indiana State School Music Association and a listing in Who's Who Among America's Teachers. She attributes much of her professional growth to mentors who modeled integrity and commitment throughout her career, and she remains most proud of the long-term relationships she has built with students, many of whom overcame early struggles to thrive later in life. Beyond her role as principal, she mentors emerging educational leaders part-time at Taylor University, has served on the executive board of the Anderson Young Ballet Theater, volunteers at Solid Rock Baptist Church, and enjoys playing piano and spending time with her family and friends.
Her Interview
Ten minutes with Jennifer
01What do you attribute your success to?
I credit my success to nearly four decades of steady growth across every level of education. I began as an elementary music teacher in Bloomington, Indiana, then taught middle and high school before moving into administration 29 years ago. That broad foundation, paired with a strong educational background — a bachelor's degree in Music Education from Indiana Wesleyan University, a master's in English from the University of Southern Indiana, an administrative supervision certification from Ball State University, and my special education certifications — has shaped the way I lead today.
02What’s the best career advice you’ve ever received?
I've been fortunate to have outstanding mentors throughout my career, including Dan Joyce, who served as principal at my current building for nearly 20 years before retiring, and Lynn Mellinger, a special education administrator who encouraged me to pursue my special education certification. Both of them modeled real integrity — they were committed to doing the right thing whether or not anyone was watching, and that lesson has stayed with me.
03What advice would you give to young women entering your industry?
I'd encourage them to stay actively involved in their professional associations — organizations like the Indiana Association of School Principals, the National Association of School Principals, the National Association of Middle School Principals, and ASCD have been valuable to my own growth. Building those professional connections and staying engaged in the broader education community makes a real difference over the course of a career.
04What are the biggest challenges or opportunities in your field right now?
The biggest challenge — and opportunity — in my role is making sure I'm showing up for every single child. Being present in this position means constantly looking for ways to make a genuine impact on each student I work with.
05What values are most important to you in your work and personal life?
What matters most to me is making a real, lasting impact on the lives of the children I serve. The achievement I'm proudest of is watching students who struggled in middle school go on to succeed as adults — building relationships and staying invested in their outcomes over time, even when they weren't always easy to reach, has been deeply rewarding. Outside of school, I stay connected to education by mentoring educational leaders part-time at Taylor University, and I've watched the special education field evolve significantly over my nearly 40 years in this work. I also enjoy playing piano at my church, Solid Rock Baptist Church, and spending time with my ten-year-old granddaughter.
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