Whispering Oak Elementary welcomes new principal

WINTER GARDEN  When Lee “Kip” Montgomery took the reins as principal of Whispering Oak Elementary School in January — replacing the school district’s principal of the year, Dr. Patricia Ramsey, who has since retired — he knew he had some big shoes to fill.

“Jokingly, everyone tells me, ‘No pressure!’” he said. “I feel blessed to have followed Dr. Ramsey, and I don’t like to use the word ‘replace,’ because you can’t replace someone of that quality.”

An avid fan of Florida State University football, Star Wars and NASCAR, Montgomery was born in Athens, Georgia, and raised in Jacksonville. Growing up, he always knew he wanted to be an educator. His mother was a teacher for 35 years, and one aspect of her job really stood out to him — the potential to impact people’s lives. 

Montgomery, who has been with Orange County Public Schools for nearly 20 years, started off by receiving a bachelor’s degree in English from Florida State University and continued on to receive a Master of Arts in teaching from Jacksonville University. Eventually, he earned his Educational Specialist degree from National Louis University.

He was happy teaching language arts and drama at Apopka Middle School for five years and had never set out to serve as an administrator until he was recommended to become a dean at Lake Gem Elementary, where he stayed for two years.

“I hope that I can mirror that success and hopefully keep Whispering Oak as a top producer of students in the county.” — Lee “Kip” Montgomery

“Once I became a dean for elementary students, I loved it, because I can see the impact of the future,” he said. “We build them for middle school, and these kids are so open and new that you can really help mold the rest of their lives. (I realized) I could either impact a smaller group in a classroom or a lot more people in a bigger role.”

He spent two years as an assistant principal at Lake George Elementary, two at Wyndham Lakes Elementary and three at Lancaster Elementary. He advanced to become principal of Southwood Elementary for the past five years, before heading to Whispering Oak.

For Montgomery, the location is also convenient because it allows him to be closer to his family — his wife of 19 years and their two sons, ages 13 and 16.

“It’s a great school, a phenomenal opportunity, it’s one of the best schools in the district,” Montgomery said of Whispering Oak. “The school has a tremendous track record of success. It’s been open for 10 years and has had high-quality A grades and had some of the best district scores. My vision is to maintain that success and momentum.”

For Montgomery, the core of education is ensuring the success of each child. 

“It’s never the same thing twice — every day is a new challenge or adventure,” he said. “It gives me the opportunity to reach a lot of different levels of people as far as education, (and to) work with parents, teachers, superintendents and the public to really bring those elements together to help kids be successful.”

One of his biggest challenges is overcoming preconceived perceptions about education, because many parents come to the school with negative views. However, his job allows him to reassure parents the school and its staff are there to help the students learn.

“Despite test scores, their kids are in a good place, and we’re doing everything to help them,” he said. “I hope that I can mirror that success and hopefully keep Whispering Oak as a top producer of students in the county.”

Contact Danielle Hendrix at [email protected].