Meet Our Team


Deborah Andersen

Reading Teacher

Deborah is a veteran reading teacher of 22 years, having worked in private schools with students ranging in age from 8-13. She has a masters in teaching from VCU and has spent her career developing thoughtful and eager readers. Another passion of Deborah’s is outdoor education and nature, so often you will see or hear of ways she is incorporating the natural world into reading studies. Deborah is excited to be part of Oakland’s amazing team of dedicated and talented teachers and staff.

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Sarah Bailey

Equestrian Program Manager and Riding Instructor

Sarah started at Oakland as an equestrian instructor in 1991 and transitioned to be the Equestrian Program Manager in 2003. Sarah is well-known and respected in the local riding community.

Prior to Oakland, Sarah assisted in classrooms that primarily served students with Autism Spectrum Disorder. Her experience in the classroom working with students with a variety of learning needs allows her to individualize and differentiate instruction at the barn.

Sarah has developed a program that allows students of varying degrees of experience to participate in the riding program building confidence and fostering success. The horseback riding curricula is built on the framework of responsibility. Closely aligned with the academic program, the horseback riding program focuses on individualized instruction, character development and challenging students to reach their potential. Sarah prepares students to participate in annual horse shows. Students often comment that if they can handle a horse, they can handle anything!

As a mother of two and an alumni parent, Sarah understands that the individual child must be appreciated and nurtured. She is excited to have both of her daughters attend Oakland Summer Camp. Although a job that requires a commitment of 365 days a year, when Sarah is not at Oakland, she can be found volunteering in her daughter’s classrooms often focusing on students that require extra attention. Sarah’s dedication to the Oakland equine program, unrequited commitment to our 16 horses, 3 goats, and 2 donkeys, and passion for teaching students with learning differences has helped change lives for over 20 years.

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Anne Gomola

Teaching Assistant

Having raised four children and working in various school settings, Anne is passionate about nurturing and educating children in the unique Oakland environment. A seasoned childcare provider, she studied at Dutchess College, is a former Piano Teacher, Girl Scout, Boy Scout, 4H leader and recently Director of an After School program.

Anne recently transitioned to Oakland as an Education Assistant and is thrilled to work with the Oakland team providing each student with the opportunity to succeed academically and socially.

Being a literacy advocate, Anne is excited to be a part of “changing lives; one student at a time”! Her motto is if you do what you love, you never work a day in your life. She is committed and dedicated to the students, supporting staff needs, and making a difference in each child’s life.

Jo Hardy

Reading Teacher

Jo is a veteran teacher with forty-two years of classroom experience. Jo has taught English on the high school level, Language Arts on the middle school level and Special Education on the elementary level. Jo joined the faculty for the summer program in 2017 and was so impressed with Oakland’s program she stayed for the winter school program.

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James Moyer

Language Arts Teacher

James is continuing a 22 year career in teaching and counseling. Jay specializes in elementary education with a focus in Language Arts and Math. He has earned two Master’s degrees in Counseling and Educational Administration. Jay is bringing his passion for education to Oakland, as well as fun pets to class, to inspire his writers. You can often see Amy, his pet chicken, along with him in the classroom.

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Chris Russo

Math Teacher

Chris Russo graduated from Hampden-Sydney College in 2003 and quickly began working with teenagers as a counselor. He has spent most of his professional career teaching mathematics and history, primarily within non-traditional academic environments, to students with learning challenges. He enjoys outdoor activities, including: canoeing, kayaking, fishing, hiking, camping, and occasionally hunting. He is also an avid drummer and has played for 26 years.

Chris joined the Oakland team during the summer of 2018 and is a welcomed addition to the school.

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Administration and Staff

Pete Cormons

Operations Director

Pete joined the Oakland team in 2013 after relocating to Charlottesville from the Washington, DC area. He spent the past 13 years as a boat Captain working on cruise Boats, offshore casino boats, tug boats, and fishing boats where he managed large teams of maritime employees, maintenance projects and vessel security. He was raised on the Eastern Shore of Virginia on a self-sufficiency farm and enjoys all things outdoors including fishing, hunting and camping.

Pete graduated from the University of Virginia in 2000 with a double major in Psychology and Philosophy. Pete’s responsibilities at Oakland include managing the maintenance team, dining facility, safety and security procedures, and the Equestrian center. He is excited to transfer his skills from the maritime industry to Oakland and improve the facilities and lives of both the students and staff he supports to make for a more positive learning environment for everyone.

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Ann Gooch


Anne graduated from the University of Virginia and became a Registered Nurse in 1987. As a nurse, she previously worked at Martha Jefferson Hospital, a local Doctor’s Office, as a public health nurse and has over 15 years experience as a School Nurse in Nelson County (five years) as well as in Fluvanna County (ten years). She started at Oakland in June of 2014. Ann lives very close to Oakland and enjoys farming her own organic food, even growing and grinding her own corn. Her work Motto is “Healthy kids are better learners!”

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Karin Holtz

Finance Director

Karin’s first experience with Oakland began as a parent. The Holtz family found Oakland as the answer to support their daughter who was struggling with academics, organization, and self-esteem. Originally only slated as a summer student, the family quickly recognized the need and benefits of the year-round program.

Today, Karin’s daughter is a successful high school student in the local public school system and the family frequently praises Oakland for her success. Karin continued her relationship with Oakland as an alumni parent and in 2007 began working as Oakland School’s Finance Director.

Karin’s responsibilities include managing SMART tuition, Oakland’s tuition management company, dorm accounts for the boarding students, and the many complex needs of the boarding and day school programs. In addition to her financial responsibilities, Karin is a key member of the book fair committee ensuring that our students have the most up to date novels and resources both for classroom instruction and personal interests.

Karin often serves as an initial parent contact for prospective families and welcomes the opportunity to share her personal story with families experiencing similar struggles. Karin is an important member of the Oakland family as is her daughter. Karin’s personal connection strengthens her passion for the program and her dedication is an asset to the Oakland community.

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Rachel McDowell

Residential Director

Rachel graduated from Virginia Tech with a Bachelor of Science in Sociology in 2013. She enjoys non-profit work and served a year in AmeriCorps,. She has worked within environmental education in West Virginia. She started at Oakland as a Residential Instructor in the summer of 2017. Rachel then continued on to become Residential Director in 2018.

Rachel focuses on building strong relationships with each student to better understand their strengths and needs. She is dedicated to working with each student to achieve their individual goals.

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Kara Presson

Admissions & Marketing Director

​Kara is a recent addition to Oakland School. From her initial contact, reading Oakland’s story and mission, she knew she wanted to bring her experience here. Kara graduated from Longwood University with a Bachelor of Science in Business Management. She discovered her love of education as a mentor with First Year Experience. Since then, she has been able to blend business and education into a career in educational administration, concentrating in higher education. Kara is excited to join the team and bring her skills to Oakland.

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Carol Williams

Head of School

Carol started at Oakland in 1978 and has held the position of Residential Instructor, teacher, Assistant Director and, since 2001, Head of School of Oakland School. She has a Bachelor of Arts in Sociology and a Master of Education in Special Education from the University of Virginia.

Carol holds a certification in special education and has instructed, mentored and encouraged students with a range of learning challenges, from mild autism and dyslexia to organizational difficulties and ADHD, for 35 years. Carol works with each member of the Oakland team and has an understanding of the unique importance of each individual as they work toward the common goal of helping students reach their potential.

Having worked in a variety of roles at Oakland she knows first-hand how boarding schools have lifelong impacts on individuals’ character, education and community. Carol is committed to fostering relationships with professionals locally and across the nation and is considered an expert in the field of individualized boarding and day programs. She frequently attends work shops, conferences, and professional development opportunities, to not only share her expertise and knowledge of Oakland but to continually increase awareness of educational trends and programs that will benefit students with learning differences.

Carol has dedicated over 35 years to children with learning disabilities and those who struggle in a traditional classroom setting. This dedication sets her apart as a renowned leader in the field of education and has been the leading factor in changing lives.

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Rashelle Williams


Rashelle Williams has a background in public service having served in the U.S. Armed Services in her field of Human Resources and Business Management. As a mother of 5 and a grandmother of 4, she is an advocate for the concept of every child being a unique person with distinct abilities and gifts. She enjoys watching the kids at Oakland gain confidence as they achieve each milestone in their specialized education plan.

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