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Director of Schools


Cindy OliveDirector of Schools

Cindy Olive

The COVID-19 pandemic caused enormous disruptions for all school districts across this nation.  One thing I have learned is we are a resilient school system, community, state, and nation! We at LCSS look forward to coming back to our school families in full in-person capacity for the 2021-22 school year!  We allowed in-person learning (if you chose to be) all year in 2020-21 for the sake of our students' learning and mental health with very few disruptions.  You should always take comfort in that all decisions are made for the best interest of your child and our community!

I am beginning my 33rd year in education with the majority of my time spent in primary grades K-5!  At Caywood Elementary, I became assistant principal in 2014 but moved on to be principal the next year. On November 1, 2017, I was named Superintendent of Lexington City School System and have loved every minute of it!  The teachers and staff here are some of the hardest working people I have ever had the priviledge of working with!

I received my BS in Ed. at the University of Memphis, my Master’s Degree from Union University and another Master’s from UT Martin. I am married to Bobby Olive and we have two children. Madison, 31, lives in Hendersonville with her hubby Nic and our first granddaughter, Miller, born July 23, 2020 and is absolutely perfect! Our son Peyton, 26, lost his job due to the pandemic and is back home regrouping. My husband Bobby and I have been married for 33 years. He has worked at FedEx for 37 years. My parents were the late Earl and Morine Haddock of Lexington.

I am very excited for this new school year!  After adjusting and re-adjusting all year through a pandemic, all I can say is "Let's do this!"