Stepping away from needing to have everything figured out was the biggest change. The path you didn't plan is often the one that leads you where you're meant to be.
Tara Lynn Chesebro · In Her Own Words
Her Story
About Tara
Tara Chesebro is a dedicated education and school business professional whose career has been shaped by her passion for mathematics, learning, and helping others succeed.
Tara began her professional journey after earning a degree in Actuarial Science. She initially worked at Sentury Insurance in Stevens Point, Wisconsin, where she quickly advanced into a management position in the pension department. It was there that she discovered her favorite aspects of the job were training new employees, solving problems, and working with Excel and data analysis. This realization inspired her to pursue a teaching license through the University of Wisconsin–Oshkosh and transition into mathematics education.
Tara spent nearly a decade teaching mathematics, combining her strong analytical background with a commitment to helping students understand and approach mathematics in new ways. She further expanded her expertise by earning a business administration license and a master's degree in Teaching and Learning with an emphasis in secondary mathematics intervention. Her graduate studies significantly influenced her teaching philosophy, encouraging her to look beyond traditional methods and explore creative, step-by-step approaches to helping students understand mathematics.
In 2025, Tara transitioned into her current role as Business Administrator for the Green Lake School District. Although the transition came earlier than anticipated, she embraced the opportunity and has enjoyed learning the complexities of school finance and administration.
In her current role, Tara combines her background in mathematics, education, business management, and financial administration to support the needs of her school district. She is a member of the Wisconsin Association of School Business Officials (WASBO) and continues to pursue professional development opportunities to strengthen her knowledge and master the responsibilities of school business administration.
Tara takes particular pride in being a lifelong learner and believes that success is not simply about the final outcome, but also about the journey, the lessons learned, and finding enjoyment along the way.
Beyond her professional responsibilities, Tara remains actively involved in supporting her school and community. She assists with student council, yearbook, and contributes to nonprofit causes, including Fox Valley Literacy, which helps children develop essential reading skills. Her commitment to continuous learning, service, and education continues to guide both her professional and personal journey.
Her Interview
Ten minutes with Tara
01What do you attribute your success to?
I attribute much of my success to my mother, who taught me the value of hard work, positivity, kindness, and always giving my best. She instilled in me the importance of treating others with respect, maintaining a positive attitude, and putting my heart into everything I do. Those lessons have stayed with me throughout my life and continue to guide me in both my personal and professional journey.
02What’s the best career advice you’ve ever received?
The best career advice I have ever received is to never stop learning and to not be afraid to take opportunities, even when you do not feel completely ready for them. Some of the biggest changes in my career happened when I stepped outside of my comfort zone and took a chance on something new.
My career path has taken me from management to mathematics education and eventually into school business administration. None of those transitions were exactly what I originally planned, but each one allowed me to learn new skills and discover new things about myself.
I have learned that you do not have to have every answer before taking the next step. Be willing to ask questions, learn from others, and trust that your experiences have prepared you more than you may realize.
03What advice would you give to young women entering your industry?
My advice to young women entering the industry is to never stop learning, trust yourself, and follow your heart. Stay open to new opportunities and growth, and don't be afraid to pursue a path that feels meaningful to you. Your career journey may not always go exactly as planned, but sometimes the unexpected opportunities can lead you to where you are meant to be.
04What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field is navigating the many laws, regulations, and constantly changing financial codes while ensuring that every decision ultimately serves the best interests of our school and students. School business professionals must carefully evaluate spending, manage resources responsibly, and stay current with frequent updates from the Wisconsin Department of Public Instruction. Balancing compliance with sound financial decision-making makes responsible financial management a constant priority.
05What values are most important to you in your work and personal life?
Family values and kindness are at the heart of both my personal and professional life. I believe in treating others with respect, compassion, and genuine kindness—values I strive to demonstrate and model every day. I also believe that the way we treat people can have a lasting impact, and I hope to create a positive environment where others feel valued, supported, and respected.
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