Floyd County Superintendent Anna Shepherd Announces Retirement

The following is a release from Floyd County Schools:

In an all-staff email that went out on Thursday morning, Anna Shepherd, Superintendent of the Floyd County Schools, announced her retirement, effective August 1, 2024. She attached a letter she had delivered to Floyd County School Board Chair, William Newsome, Jr., and Vice Chair, Linda C. Gearheart, along with a note of gratitude.

Among her many accomplishments over the past three years, Superintendent Shepherd was named Jobs for America’s Graduates (JAG KY) 2024 Superintendent of the Year. She is also a member of Kentucky Women in Education Leadership (KWEL), served as a panelist this year at the Leading Ladies Conference, and had her life story featured in the children’s book “Bluegrass Bold.” Superintendent Shepherd cemented her leadership ability early-on in her tenure by building numerous community partnerships and securing support statewide during the Eastern Kentucky flood in 2022.

As she reflects on her time leading the Floyd County Schools, Superintendent Shepherd is most proud of being a “Students-First” Superintendent. She has encouraged and celebrated student accomplishments through handwritten note cards and newspaper clippings mailed to their homes, has attended as many sporting and academic events as her schedule would allow. She has also instituted listening sessions with students, a new priority, empowering them to speak up about and envision the change they would like to see in their school communities.

During her three-year tenure, she has held lunch and learns with students (and also listen and learns with school administrators). She celebrates students who score 30+ on the ACT by treating them to dinner with her and initiating them into the Superintendent’s 30+ Club. During high school graduations, graduates receive encouragement cards and notes of support from all school employees.

Annually, students design the yearbook cover and the Superintendent’s Christmas Card set. New CTE pathways are considered and added, based on student feedback – this year aerospace and theatre are new additions. Floyd County students also participate in College Now/College 101 for 9th graders to engage them in the college experience along with a dual college academy with tutoring and homework help through university partnerships.

Participation alongside students in the Local Laboratory of Learning initiative with the Kentucky Department of Education (KDE) and United We Learn has included student development of a Profile of a Graduate and a Digital Portfolio. She has developed a Career and Technical Pathway Catalog and videos with a look inside each pathway so students and families can dream big with and for their children and grandchildren.

Mrs. Shepherd has prioritized huge investments in the arts on behalf of her students at a time when other districts are making cuts to the arts. This has been achieved through purchases of instruments for K-12 students and a growth in band participation, via field trips for preschool through 12th grade to the Mountain Arts Center so that they can experience the arts and dream of performing on stage there or cultivate a lifelong appreciation of the arts as a future patron.

Mrs. Shepherd initiated service pin awards for employees to celebrate their years of dedicated service to students and families. In collaboration with community champions, she has expressed gratitude to her team by providing lunch to all Floyd County Staff on closing day each year. To help staff reflect, inspire, uplift, and focus on the positive, she sends Monday and Friday Morning Mindsets which is a set of quotes to start and end the week together. Over the past 3 years, Floyd County Schools has had a focus on social-emotional learning and youth mental health. All 1,020 staff have been trained to best serve student and adult needs over the past 3 years.

Although she is the first female Floyd County Superintendent, she knows she will not be the last. Mrs. Shepherd celebrates staff births and adoptions by sending “Future Superintendent of Floyd County Schools” onesies, regardless of gender.

This year, she secured $600,000 in funding in collaboration with Senator Turner and the Kentucky General Assembly for upgrades to the Floyd County Area Technical Center, the second oldest Area Technology Center in the state that is in desperate need of a complete renovation.

Mrs. Shepherd holds herself and others to a high standard, values feedback, and believes in continuous improvement. She has emphasized this by initiating advisory councils for students, community, classified and certified staff. She spearheaded the development of a strategic plan for the district that included a revision of the district’s mission, vision, motto, and key verbs (Engage, Empower and Equip) to drive its work with collaboration and involvement through advisory councils from all stakeholders.

Soon, the new Floyd County Transportation Department building will open, following a fire that destroyed the previous bus garage. And because safety is her number one priority, she has added 21 new buses to Floyd County’s fleet in 3 years. The new STEM bus should debut in July and a new Pre-School bus on wheels has been purchased to travel out to neighborhoods to increase kindergarten readiness for the 3–5-year-olds not enrolled in a formalized childcare setting within their communities.

As an additional commitment to safety, under her leadership, the Floyd County Schools has secured and funded positions for 13 School Resource Officers for each of its 13 campuses in partnership with the County Sheriff’s Dept. and the City of Prestonsburg. This measure is one of the things that Mrs. Shepherd is most proud of, as the safety of students and staff is paramount.

Mrs. Shepherd has selected a theme for staff and students during each year of her tenure to guide their work and success. She hopes all district staff have internalized the three messages and will use these platforms to build upon their future aspirations and endeavors for continued personal growth and professional success.

Year 1: Rowing and Growing Together to WIN for our students, families, and communities. (Inspired by the book, “Row the Boat” by Jon Gordon and PJ Fleck.)

Year 2: The Butterfly Effect: Every Single Thing You Do Matters Forever. (Inspired by the book, “The Butterfly Effect: How Your Life Matters” by Andy Andrews.)

Year 3: One person can and does make a difference in the life of a child, a family, a colleague, and a community. (Inspired by, “The Starfish Story.” Also inspired by Dr. Chandra Varia, after the flood, sharing with staff that we each have 2 hands and if we 1,020 employees each use them to help one family the impact that would have on our community would be tremendous.)

Mrs. Shepherd raised her daughter in Floyd County and got her start as an educator teaching kindergarten at Prestonsburg Elementary, before transferring to May Valley Elementary where she also taught kindergarten. She then spent three years as a district curriculum resource coordinator at Allen Central High School. Next, she was selected to spend three years at the Kentucky Department of Education as a Highly Skilled Educator, serving districts all across the state, before returning to Floyd County to serve as a Gap Coach for High Schools. Immediately prior to becoming superintendent, she spent eleven years as the Chief of Early Childhood at the Floyd County Schools.

Although Mrs. Shepherd has not formally announced what may be next for her beyond retirement, she has indicated that her passion for education and advocacy on behalf of students will not end when this chapter closes. In fact, she believes she may be even more impactful and engaged as a private citizen in the months ahead. For now, she pledged to ensure a smooth transition to the next interim or superintendent to take the helm at the Floyd County Schools.