How Caldwell academy turned scheduling into an iterative process

In late April 2026, about two months before the term, a teacher at Caldwell Academy requested to go part-time and teach only in the mornings. For years, that single request would have forced the team to rebuild the entire schedule by hand. This year, Elizabeth Gilbert (Liz) opened ScheduleX, changed the teacher's classes and availability, and re-ran the schedule. The result caught her off guard. The new version came out better than the one it replaced, with higher fulfillment.

That moment captured a much bigger shift. The team was no longer locked into the first schedule that worked. They could make a change, visualize its impact, understand the trade-offs, and make an informed decision about what the final schedule should look like.

The School

Founded in 1994, Caldwell Academy is a classical Christian day school in Greensboro, North Carolina, serving 576 students from Pre-K through Grade 12. ScheduleX supports scheduling for 285 middle and upper school students across 148 course sections. The school recently transitioned from Blackbaud to Veracross as its student information system.

The Challenge

For years, Caldwell built its schedule by hand on a whiteboard in the principal's office. Finding a version that worked took weeks. But time was only one problem.

The bigger challenge was that the team could only afford to build one schedule. Once they found a version that worked, they stopped exploring other possibilities because testing another approach meant investing weeks of work all over again.

Caldwell's structure made that challenge even harder. For example, most rising junior classes offer only one section of most core courses (singletons), including Literature, AP Literature, Physics, and Honors Physics. One student's course request can ripple through the rest of the schedule, affecting the options available to everyone else. When so many decisions are interdependent, finding a workable schedule is difficult. Finding a better one is even harder.

This left the team no flexibility if circumstances changed after finishing the final schedule. If new students enrolled over the summer or a staffing change happened in late June, rebuilding the schedule simply wasn't an option. As Liz puts it, they were "kind of locked in" to what they had already created. This impacted students too - when scheduling conflicts prevented students from getting the classes they requested, the team had to ask them to choose alternatives instead. As Liz describes it, "the worst part is when you do have to go back to a kid and be like, okay, well, we couldn't give you this. What would you want as a second choice?" Some summers, those conversations extended to parents as the school worked through changes in June and July.

The process was also fragile. One time, after the team finished the schedule but before anyone had written it down, the facilities crew accidentally wiped the whiteboard during routine cleaning. With no backup, the team had no other option but to rebuild the entire schedule from scratch.

From one Schedule to Many

ScheduleX changed how Caldwell built its schedule. Instead of spending weeks trying to arrive at a single workable version, Liz could generate a schedule, evaluate the results, adjust a constraint, and run it again. What once required starting over from scratch now took only a few hours, making it practical to explore multiple options before deciding on the best one.

Liz no longer had to trace the impact of a scheduling change by hand. She could move between student, teacher, course, and schedule views to understand the consequences of every decision as she refined the schedule.

"I love that I can look at the schedule in five different ways," Liz says. "I can search by student, I can search by course, I can search by teacher. I love that it works."

The Impact

Running multiple scenarios revealed that some of the school's biggest constraints weren't constraints at all. "I thought, okay, we need two sections of Honors Chemistry and two sections of Latin," Liz says. "It's never going to work if we don't have that." But when she tested that assumption, ScheduleX fit both courses into a single section. "I was shocked."

Reducing those courses from two sections to one freed up meaningful capacity for two teachers who had been carrying particularly heavy teaching loads. In total, Liz and her team built around 15 different schedule scenarios, exploring the tradeoffs behind each one. That kind of experimentation would have been impossible if they were still building the schedule by hand.

Those discoveries also improved what mattered most: getting students into the classes they requested. Caldwell fulfilled 1,794 of 1,798 course requests, achieving a 99.78% fulfillment rate with only four requests left unmet. All four belonged to the junior class, where most courses run as single sections and flexibility is especially limited. Reaching that level of fulfillment would have been nearly impossible with the school's previous manual process.

Building schedules faster wasn't the biggest change. Building them without starting over every time was. When a last-minute staffing change required a teacher to move to mornings only, the team updated the constraints and generated a new schedule within a few hours. "We did not feel the stress of being locked into a schedule at any point," Liz says. The schedule stopped feeling permanent. It became something the team could revisit, refine, and improve whenever circumstances changed.

Looking Ahead

With the pressure of simply producing a schedule behind them, Liz and her team are now thinking about questions they never had time to ask before. Next year, they plan to explore teacher room sharing to make better use of limited classroom space and let ScheduleX assign rooms automatically. They also want to revisit common planning periods, a goal they postponed this year because they were balancing too many constraints at once. Balancing class sections by gender is another priority.

The team's focus has shifted. Scheduling is no longer just an annual task to complete. It has become a planning tool that helps Caldwell make better decisions about how the school operates.

Liz's Advice to Other Schools

Before choosing ScheduleX, Liz spoke with schools already using the platform. Their recommendation gave her the confidence to move forward. Today, she offers the same advice when other schools reach out to her.