Jennifer Gill’s children were in middle school when she accepted the job to be the District 186Â superintendent in 2014. Now, her kids are in college, and Springfield schools have changed over the decade of her leadership.
Gill has worked as a teacher, principal and administrator in Springfield schools since 1994. Her superintendent contract ends after the 2026 school year, and she isn’t ready to decide if she’ll continue.Â
“I’m not looking to the future beyond this right now, because I’m right in the middle of serving this district,” said Gill, age 54. Â “I don’t think my age is in question to anybody but in due time, I’ll announce my next steps and talk about that a little bit more.”
In 2023, Gill received a two-year contract extension and pay raises to be implemented by the end of 2025. Her salary is $209,664, up from $195,000 in 2014 when she was hired. She is now one of the highest paid superintendents in central Illinois, according to Illinois Board of Education data, and needs to negotiate her salary for the 2025-2026 school year by March 1, 2025.
A decade of reappointment: stagnant or stable?
Gill took office in an unsteady time for the district, when her predecessor, Walter Milton, left under a controversial settlement agreement. The district had a projected $5 million deficit, a lack of minority teachers and the need to implement a new statewide curriculum.
Community members wanted more stable leadership at the time.
“The stability of having someone in here on a more permanent basis is going to be great,” Karen Stapleton-Crump, principal at Jefferson Middle School, said at the time. “I don’t think, I know, that is what our district needs.”
Years later, Gill’s contract has been renewed three times, and a few members have warned against stagnant leadership. Current board president Micah Miller voted against the three-year extension in 2023, expressing frustration with graduation rates and test scores.
“While I appreciate her service and her energy, I am keenly interested in what a fresh perspective could bring the district,” Miller told Illinois Times recently, clarifying his 2023 stance. “My no vote was to not offer any extensions past the 10 years, because I am eager to see what that new vision can bring to our students, families and teachers.”
In 2017, longtime and now retired board member Judith Johnson voted against Gill’s five-year contract extension, advising against contracts over three years during uncertain financial times.
How has the district changed under Gill’s decade?
In 2017, Sangamon County voters passed a school tax referendum that funds an average of $13 million to school facility improvements annually. Gill says this is her biggest accomplishment.
“We needed additional space in many of our facilities, and we needed to improve upon the space and the learning environment,” said Gill. “So that has been a huge challenge to attack all of those things, but it’s a true gift from our community for giving us public permission to do that work by saying yes to the 1% sales tax.”
At the time, there were 25 mobile teaching units, according to Gill. Now, those have been eliminated. The tax has funded a $93.2 million reconstruction of Lanphier High School, renovations at Springfield High School, new athletic facilities, cafeterias and more.
The tax has also helped ensure all schools now have double-door entrances, according to Gill.
And after a few safety threats, the school board voted in 2022 to use the tax funds to install metal detectors in schools.
The most recent security addition came from the Elementary and Secondary School Emergency Relief funds. Teachers now carry security badges with emergency call buttons for staff. The calls are sent to the main school office.
Room for improvement
Gill says the COVID-19 pandemic was the hardest challenge of her career.
“It was a disruption that was two years long, and it’s taken us about two years to dig back out of that hole and do the right thing for kids,” said Gill.
Since the pandemic, Gill has noticed an increased need for social-emotional learning.
“We’ve adjusted our curriculum to have opportunities to teach skills around social-emotional learning and how to be a good friend, and how to focus on making sure everybody has a sense of belonging and coming out of COVID,” said Gill.
Ken Gilmore, school board member for sub-district four, says the board is also concerned about topics such as the district’s new phone policy and academics, especially after graduation rates and testing scores were down in 2023 according to the ISBE Report Card.  Â
And in the background of the district improvement work is its $20 million deficit. The ESSER pandemic relief funds ended Sept. 30, 2024.
“We are scrutinizing our spending now so that hopefully we won’t have to make such painful cuts or such noticeable cuts, that we can keep the best of some things and still move forward in a productive way, but not to the width of what we had been moving,” said Gilmore.
Looking forward
Gilmore says the board will begin the detailed superintendent evaluation process in 2025.
“The evaluation is a pretty important piece, and that’s where you determine whether they can continue, or you’re going to give them another year or two or make a plan for improvement,” said Gilmore.
Gill is waiting to announce her next steps, but she knows she wants to stay in the area.
“I don’t know if I would have ever applied for a superintendency if this one had not come open,” said Gill. “I’ve met so many great people in our community that they give back in so many ways. This community really works for District 186 and helps us thrive in so many ways, and I’m so appreciative of that. The opportunity to serve the place I’ve lived my whole life is so cool.”
Gill is a lifelong resident of Springfield and graduate of Springfield Public Schools. She received her master’s degree in Educational Administration from University of Illinois Springfield and serves on six local organization boards.
She wants to continue helping the district “level up,” a phrase she coined from her current favorite book, Leveling Up, by Ryan Leak.
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