He left athletics for academic when he became principal at Harrodsburg Middle School in 1993.
“I went right out of the classroom and into principal,” he said. “And that’s kind of how I got to here. Just kind of went from there.”
After Harrodsburg Middle School, he became the principal of Hogsett Elementary School for three years before applying for the superintendent position at Burgin Independent Schools.
According to Webb, most places he went were rebuilding at the time of his arrival, and Burgin was no exception.
“We needed to make some changes,” he said. “Things weren’t working as well as they should have. We were losing students ...”
Webb said he is not better than his predecessor, but emphasized the need for rebuilding.
In particular, the budget needed to be expanded, and the school needed to find a way to keep students. As of 2012, the budget was $3.3 million, up from $1.5 million in 1998, and student numbers also are up, so much in fact that a waiting list for the school has been frozen.
Before Webb came, there was talk of consolidation with Mercer County, according to Burgin principal Marty Collier.
But since Webb helped improve the budget so quickly and helped student numbers steadily increase, Collier said she hasn’t heard talks of merging since.
“I¿was impressed with how he turned the school system around so quickly,” she said.
Collier said it was this handling of the budget, which allowed for more teachers, that was the most important thing Webb changed for the school.
Another change made by Webb that affected Collier personally was the reconfiguration of the system’s middle school. Initially, the middle and high school shared teachers and curriculum, and Collier believed her first son struggled because he was immediately treated like a high school student. But under Karen Girard, the former principal, and during Webb’s second year as superintendent, the middle school became its own section with its own content area teachers.
“That made such a huge different for my second son,” she said. “There’s no transition issue, that was a big deal.”
Collier said one thing that makes Webb unique is that the school setup allows him to visit students and classrooms frequently, and that he knows most students by name.
“That is a rarity,” she said.
Webb said this part of the job is unique.
“The fact that I have the opportunity to influence education on an individual level on a daily basis is unique,” he said. “Cause we’re small and unique. We don’t compete with anybody but ourselves.”
Bob Clark, chairman of the Burgin Board of Education, praised Webb for his years of service.
“As chairman of the board I am very pleased with the results Dick has attained in his 15 years,” he said. “He is an asset to the school.”
Webb said he’s heard that a person knows when it’s time to retire, and so far he’s not felt the urge.
“I plan on working as long as I continue to enjoy it,” he said. “(I hope) that I can continue to be a viable part of the process.”