Amanda Callaway of Oregon CUSD 220 named 2025 Holly Jack Award Winner
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Date PostedOctober 15, 2025
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CategoryNews
Amanda Callaway, administrative assistant to the superintendent and board of education and district office manager for Oregon CUSD 220, has been named the winner of the 2025 Holly Jack Outstanding Service Award.
The annual award recognizes administrative professionals and board secretaries for performance, initiative, innovation, passion, staff development, and dedication to the district, community, and students. Callaway will be recognized in front of peers on November 21 as part of the opening session of the Administrative Professionals’ Program at the Joint Annual Conference in Chicago.
Nominations were made by district superintendents and school board presidents. Letters of support from the CUSD 220 superintendent, board president, and fellow district office staff spoke of Callaway’s humility, problem-solving ability, and deep commitment to public education. Oregon CUSD 220 Superintendent P.J. Caposey, Ed.D., referred to Callaway as the foundation of the office and a reliable, steady hand that leads with confidence, high expectations, and relentless excellence.
“Mandi has more skill, more tenacity, and more leadership instinct than anyone I’ve ever worked with in this role,” Caposey emphasized. “What makes Mandi extraordinary isn’t just her ability to do hard things — it’s her ability to lead through them. She mentors a group of high school students who serve as our communication interns, guiding them as they grow professionally and personally. That heart for students still drives everything she does. She does it all with precision, humility, and a deep commitment to public education. I can’t think of anyone more deserving of this honor.”
Speaking to fiscal challenges and recent staff turnover in the district office, Oregon CUSD 220 Board President Bryan Wills said, “Mandi showed true leadership and dedication over the past year helping the district through a very long and difficult administrative transition and financial crisis. In addition to navigating the financial turmoil, Mandi also completely trained and onboarded the entirety of the district office staff, ensuring a smooth transition and operational consistency. Mandi Callaway has, and will continue, to play an integral part in the success of our district, our kids, and our community.”
Amanda Callaway has served as the executive assistant to the superintendent and CUSD 220 Board of Education for five and a half years, while also leading the district office. Callaway previously served in the district as a classroom paraprofessional and interventionist.
Oregon Junior/Senior High School Principal Heidi Deininger commended Callaway’s deep-rooted commitment to staff and students, and her passion for work in public education. “Mandi is a team player who fosters a positive and supportive environment. Her kindness and compassion shine through in every interaction, making her an invaluable resource to colleagues, administrators, and community members alike,” said Deininger. “She embodies the very best qualities of a leader, team player, and advocate for education, making her a truly deserving recipient.”
The Holly Jack Outstanding Service Award is named in memory of a long-time Illinois Association of School Boards employee, Holly Jack, who served as an IASB Field Services (now Outreach and Training) administrative assistant and was instrumental in promoting and developing professional development programs for board secretaries. The award recognizes the dedication to service and extraordinary contributions of administrative professionals who serve and assist their local boards of education.
The annual award recognizes administrative professionals and board secretaries for performance, initiative, innovation, passion, staff development, and dedication to the district, community, and students. Callaway will be recognized in front of peers on November 21 as part of the opening session of the Administrative Professionals’ Program at the Joint Annual Conference in Chicago.Nominations were made by district superintendents and school board presidents. Letters of support from the CUSD 220 superintendent, board president, and fellow district office staff spoke of Callaway’s humility, problem-solving ability, and deep commitment to public education. Oregon CUSD 220 Superintendent P.J. Caposey, Ed.D., referred to Callaway as the foundation of the office and a reliable, steady hand that leads with confidence, high expectations, and relentless excellence.
“Mandi has more skill, more tenacity, and more leadership instinct than anyone I’ve ever worked with in this role,” Caposey emphasized. “What makes Mandi extraordinary isn’t just her ability to do hard things — it’s her ability to lead through them. She mentors a group of high school students who serve as our communication interns, guiding them as they grow professionally and personally. That heart for students still drives everything she does. She does it all with precision, humility, and a deep commitment to public education. I can’t think of anyone more deserving of this honor.”
Speaking to fiscal challenges and recent staff turnover in the district office, Oregon CUSD 220 Board President Bryan Wills said, “Mandi showed true leadership and dedication over the past year helping the district through a very long and difficult administrative transition and financial crisis. In addition to navigating the financial turmoil, Mandi also completely trained and onboarded the entirety of the district office staff, ensuring a smooth transition and operational consistency. Mandi Callaway has, and will continue, to play an integral part in the success of our district, our kids, and our community.”
Amanda Callaway has served as the executive assistant to the superintendent and CUSD 220 Board of Education for five and a half years, while also leading the district office. Callaway previously served in the district as a classroom paraprofessional and interventionist.
Oregon Junior/Senior High School Principal Heidi Deininger commended Callaway’s deep-rooted commitment to staff and students, and her passion for work in public education. “Mandi is a team player who fosters a positive and supportive environment. Her kindness and compassion shine through in every interaction, making her an invaluable resource to colleagues, administrators, and community members alike,” said Deininger. “She embodies the very best qualities of a leader, team player, and advocate for education, making her a truly deserving recipient.”
The Holly Jack Outstanding Service Award is named in memory of a long-time Illinois Association of School Boards employee, Holly Jack, who served as an IASB Field Services (now Outreach and Training) administrative assistant and was instrumental in promoting and developing professional development programs for board secretaries. The award recognizes the dedication to service and extraordinary contributions of administrative professionals who serve and assist their local boards of education.
