Meet Our Staff

Michael & Toby Gress:

VMS is owned and operated by Michael and Toby Gress, certified Montessori teachers and graduates of the University of South Florida.

The Gresses hold degrees in Elementary and secondary education. They are MACTE accredited Montessorians with affiliations to M.E.P.I., NAMTA, AMS, and I.M.C.

The Gresses’ Montessori training took place in Tampa, Fla. directly under Dr. Helen K. Billings, the founder of the Montessori Institute of America. She instilled in all of her protégés a deep conviction that the Montessori Method, properly approached and applied, would greatly benefit the whole life of the children under their care. This love for the child and the man or woman they would become has grown over the years. Currently, the Gresses are under the mentorship of Joan Parasine, Founder and Head of School at Montessori School of McLean, an AMS Accredited school and one of the oldest Montessori schools in the Washington area.

Cindy Hessler


Cindy, a mother of two teenage children, joined the VMS Community in March of 2007, when she began working as a Primary classroom assistant. She has completed Classroom Leadership Studies with The Montessori Foundation as well as numerous workshops with Montessori educators. She has loved watching our students grow and develop through the Montessori approach that develops all facets of the whole child.

After three years as a Classroom Assistant, she began to transition into the excellent School Administrator she is now. She quietly keeps the information and paperwork flowing smoothly, while still helping out with Carpool, Playground duties, and assists in the classroom when the necessity arises.

Originally from Western New York, she participated in several overseas exchange programs that inspired her to complete her B.A. degree in International Relations and German from Canisius College. In addition to her “global” mindset, Cindy brings to the VMS Outdoor Classroom over ten years of outdoor nature experience, leading and mentoring youth as a Boy Scout assistant scoutmaster and camping guide for the Girl Scouts.

Shoshana Montgomery

Administrative Assistant

Shoshana received her bachelor’s degree from James Madison University with a double major in Library Science and Speech and Drama. She began her working career as a Children’s Librarian in Fairfax County, Virginia and loved it for the four years she was there. She taught the children how to research, engaged them in cultural activities such as folk dancing, and had them help decorate the library with tie-dyed curtains they made themselves.

That was followed by 10 years raising her three daughters in Reston (“the biggest job ever!” she says.) When the time came to work out of the house, she found a home with CH2M Hill in Herndon, helping them to establish their technical library and assisting the research of their engineers and scientists. For many years thereafter, she supported various technical companies as a contract administrator and records manager, putting her organizational skills to good use on numerous proposals large and small. When she retired from Northrop Grumman, she began pursuing her creative passion for designing jewelry and fabric art, which she sells on Etsy and at the Bluemont Fair.

Shoshana supports the wonderful work of VMS in its pursuit of accreditation and the massive documentation that is required to accomplish that task. She also supports Toby and Cindy Hessler in day-to-day administrative tasks on a part-time basis. “This is a great place to observe the fascinating growth happening everywhere on the VMS property,” says Shoshana. She lives in Sterling, Virginia where she is working on establishing an area of native plantings for her neighbors to enjoy..

Victoria Stephens

Lead Elementary Directress

Mrs. Stephens is originally from Nashville, TN. She received her bachelor’s degree from David Lipscomb University (a small Church of Christ college in Nashville) with a major in elementary education. She received her master’s degree from Vanderbilt University with a major in special education.

She began teaching in the fall of 2000. She taught for nine years in Loudoun County, three years in special education and six years in third grade. She started teaching at VMS in the fall of 2012. She is a certified Montessori teacher and has held a Virginia teaching certificate for over twenty years.

She lives in Northern Virginia with her husband, Peter. They have two children. Bethany works as a photographer’s assistant in Falls Church, and Warren attends NOVA Community College.

Anni Bryner

Tender Twos and Stepping Stones Teacher

Angela Bryner leads VMS’ Tender Twos and Stepping Stones programs. She also assists in the primary classroom and leads art and drama programs in both the Primary and Elementary classrooms. She is an AMS Certified Montessori teacher and multi-media artist who has been working with children ages 2-18 since 1993. After receiving her training through Northeast Montessori Institute, she began working with Toddlers ages 18 months to 3 ½ years in addition to teaching art and drama to preschool and elementary students. She holds a B.S. from the University of Virginia in Archaeology with an art history concentration, and has been a Lead Toddler teacher in Northern Virginia for the last several years. Other experiences include teaching and designing materials for Charlottesville’s Discovery Museum, leading archaeology camps for the National Wildlife Federation’s Eastern Wildlife Camp, volunteering for two years as a Girl Scout Brownie leader, and traveling Northern Virginia as a puppeteer and storyteller with Barnes & Noble. Mrs. Bryner has also taught numerous jewelry, textile, art history, painting, and clay classes to both children and adults for the past several years at Potter’s Wheel Studio. In addition to her love of working in a Montessori classroom, she is an avid reader, weaver, painter, knitter, spinner, jewelry artist, and also enjoys carving her own rubber stamps. She recently moved to Round Hill, VA with her husband and an assortment of rescued dogs and cats.


Alissa Westrick

Lead Primary Directress

Alissa’s journey includes over 17 years of work with children, youth, and adults, assisting with county and public school programs and counseling services. She received her Masters of Education in School Counseling, Pre-k through 12, from Virginia Tech, and a Bachelors of Science in Social Work from Slippery Rock University. Alissa is a certified I.M.C. Montessori Primary Directress (Guide)

Today, Alissa has the honor of lovingly guiding the primary class at VMS. She found VMS through her calling to help others discover and nurture their individual gifts, which brings out the best in our children. “They are the foundation,” she says, “the ‘it’ of everything! They are our direction towards the meaning of life and the shape of our future.”

Like many of the VMS staff, reading “Maria Montessori: Her Life and Work” was a transformative experience. “The Montessori method,” says Alissa, “is not only a way of educating, it is a lifestyle. Her life’s works instill in me a sense of peace as well as an intentional way of being. Her knowledge and information provide important insights into kindness and respect for human life.” Which has informed my classroom management style.

Caroline Malone

Elementary Classroom Assistant

Caroline joined the staff of VMS in 2014 after participating as a parent since 2011. She has two children in the program, one in primary and one in elementary. It has been an absolute joy for her to engage with the students, staff, and families on a daily basis as her understanding of the Montessori practices and methods grow. She has a BS in Biology from the University of Mary Washington and a BS in Nursing from Georgetown University. After graduating from Georgetown in 2002, she worked as an RN at Children’s National Medical Center in Washington, DC until she had her daughter in 2007.