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Our Team

Our Leadership Team

With the help of teachers and the environment as the third teacher, students
have opportunities to confidently take risks.

Jessica Kent

Co-Founder & Director

Jessica Kent is the Co-Founder and Director of Watermark Homeschool Enrichment, where she is able to connect passionate professionals with homeschooling families. Jessica and her husband Joel, are proud parents to eight wonderful children and have enjoyed homeschooling their crew since their oldest child was in preschool. She holds a BA in American Sign Language – Educational Interpreting, from the University of South Florida. Although, family, homeschooling, and Watermark take most of her time she has a love for all things Jesus, Disney, scrapbooking, and Chic-fil-a Sweet Tea!

Born and raised in Orlando, Jessica & Joel have also set down roots in Central Florida and love raising their children in the Florida sunshine.

Christie Winkler

Assistant Director

Christie Winkler serves as the Associate Director of Watermark, where she works alongside Jessica and pesters her for practical homeschool and housekeeping ideas when they’re not talking Watermark stuff. Christie and her husband, Chris, served with Wycliffe Bible Translators in Nigeria before moving back to the States to work in Wycliffe’s Orlando office. They are currently stumbling through parenting their three children and grateful that God’s grace is greater than their knowledge and patience. She and her husband have a heart for authentic community and seeing the beautiful diversity of God’s kingdom celebrated. In her Life Before Homeschooling, Christie worked as a children’s minister and taught high school English. When she isn’t enforcing timeouts, figuring out how her kids doing chores can be turned into a Home Economics assignment, or hiding in the bathroom, Christie can far too frequently be found at book sales or thrift stores feeding her (and thankfully, her family’s) love of reading by searching for discarded literary treasures to fill their bookshelves.

Vanessa Ramirez

Leadership Admin

I was born in Puerto Rico and lived on the tropical island for 35 years. I am married to Felix Ocasio and the mother of two beautiful girls, Sophia Ocasio who is 12, and Amaya Ocasio who is 7. In 2012, we moved to Jupiter, FL due to a job opportunity. During our time in Jupiter, my husband and I decided we wanted to homeschool our older daughter who was going into the second grade. We were looking for flexibility and we also wanted to be part of her education and offer her opportunities that we knew she wouldn’t have at normal public schools. In late February 2018, we decided we wanted to be close to family and friends, so we moved to Lake Nona in Orlando. In search for co-ops to support my daughters’ education, we came across Watermark Homeschool Enrichment, and we have been part of it since Watermark was formed. As a former Registered Nurse, I don’t regret staying home with my daughters and being part of their educational journey. As a family, we love to spend time together, spend time with family and friends, and to travel. In May 2020 I became part of the leadership team at Watermark Homeschool Enrichment, and I’m really looking forward to see Watermark grow.

Cynthia Ramirez

High School Coordinator

Cynthia has been homeschooling her two sons since 2014. After things weren’t going well in the public school system she decided to start homeschooling. Homeschooling has given her the opportunity to combine different educational methods along with unit studies and game schooling, therefore, creating an environment where her sons flourish. Although homeschooling is a huge part of her life she also loves to spend time with her beloved husband and boys traveling, enjoying the local theme parks or watching a good movie. Watermark has been a blessing as her and her boys enjoy the community feeling, passionate teachers and great friendships that have been made.

Joy Clifton, M.S.

Board Member/Financial

For over a decade, Joy has worked with adolescents and children in the mental health field. Through private practice, the Department of Juvenile Justice and currently with the public school system, Joy provides counseling services for mental health and substance abuse needs to various populations. She is also an Ordained Minister in the Church of God and has served in the local church as a staff pastor and alongside her husband Nolan in various positions. Joy is grateful to be a part of the Watermark family. She has previously served Watermark families as a teacher and currently supports as a member of the Board of Directors and with finances. She and Nolan live in Orlando, Florida with their two-year-old daughter Hope.