Teacher Feature: Mrs. Winfrey and Mr. Smith

Last winter, the pandemic turned our world upside down and left all schools in the precarious position of having to figure out how to continue delivering meaningful instruction despite being physically separated. Thanks to the efforts and expertise of Director of Technology Sharon Winfrey and Technology Support Specialist Benjamin Smith – who are the collective focus for today’s Teacher Feature – Old Trail was able to pivot quickly to distance learning last spring. 
The team then led the way again as we planned to engage students both on and off campus this fall.

“Sharon and Ben are deserving of this honor because of all the work they do behind the scenes that goes unnoticed by many of our parents,” said Grade 4 teacher Dean Ruff. “Without them, we would not have been able to transition back and forth so seamlessly. It would have been a mess!”

Long before the decision was made to close school last March, the tech team began preparing for the possibility. They reached out to organizations like the International Society for Technology in Education (ISTE) and the Association of Technology Leaders in Independent Schools (ATLIS) to find resources to provide online learning tools.  

“We didn’t know what to expect since we had never experienced anything like this before,” Mrs. Winfrey said. “But I believed that we would work it out together and do whatever was needed to support our faculty, staff, students and their families. I could feel the understandable apprehension of our teachers since they would be the ones on the frontline, but I've seen their dedication to their craft and knew that they would find a way to make this work for our students.”

Mrs. Winfrey has been at OTS for 24 years, including the last 20 in her current position. In all, her experience in the tech field dates back to 1983. She said the most fulfilling aspect of her job at OTS is the “opportunity to explore the many areas of technology and to help wherever help is needed.” In addition to her tech responsibilities, Mrs. Winfrey plays an essential leadership role at the school as an administrator, but that’s not all. 

“There are times when I’m a director; a network administrator; a technician; a computer science teacher; a traffic cop; a track coach; an advisor; an affinity group leader; a participant in diversity efforts; a temperature reader; a receptionist; a chaperone; an application programmer and designer; and so on,” she said.

Away from school, Mrs. Winfrey enjoys landscaping, her pink nose pitbull named Pearl, and visiting campgrounds across Ohio in her 36’ RV camper. She has also owned four motorcycles in her life, including a Kawasaki Ninja sportbike. 

Mr. Smith, who is in his fourth year at OTS, has always had a passion for all things technology. 

From a very young age, I had a desire to understand how things worked, which often resulted in breaking things as I took them apart,” he said. “Working in the technology field both fulfills my passion for understanding the inner workings of things, and also has given me the skills needed to fix things, instead of just breaking them.”
Mr. Smith manages the school’s tech support ticketing system and is often the first responder when issues arise. He also keeps track of all the school’s computers and devices.  

I love the diversity in what I do – no one day is ever the same,” Mr. Smith said. “Being in education gives me the opportunity to explore many technologies that I would not get to experience working somewhere else. Additionally, I love having the opportunity to share my knowledge with students.”

Although his passions away from the job remain immersed mainly in technology, he also enjoys taking camping trips to unplug and is an avid reader. He’s also very interested in anything that has to do with space and space travel, and one day hopes to have the opportunity to visit space!


#TeacherFeatureFriday is a series that aims to help the OTS community get to know our faculty and staff better. On select Fridays throughout the school year, we will use this space to highlight some of the amazing individuals who make Old Trail such a distinctive place for children to learn and grow. Past Features: Dean Ruff, Grade 4 Teacher, Sept. 25, 2020; Rachel Rich, ECP Teacher, Sept. 11, 2020.  

Old Trail School is a private day school for preschool through grade eight students located in Cuyahoga Valley National Park.