Dr. Wollensak began his career with a bachelor of science degree from the University of Vermont in 1982. After graduation, he went on to work in immunological research at Forsyth Dental Center in Boston. It was his experiences at Forsyth, studying ways the bodys immune system works against the causes of dental disease, that led him to attend Loyola University School of Dental Medicine in Chicago. During his years in dental school at Loyola, where he excelled in clinical dentistry, he was selected to practice in the oral surgery honors program and was awarded for excellence by the American Association of Oral and Maxillofacial Surgeons.

After receiving his Doctor of Dental Surgery degree in 1987, Dr. Wollensak returned to Vermont and began a general practice residency at the UVM medical school. During this residency he received advanced training in general dentistry, treating medically compromised patients, oral surgery, and anesthesia. In September 1988 Dr. Wollensak began private practice in Barre, Vermont. For many years while in private practice dental residents from the general practice residency at UVM rotated through Dr. Wollensaks practice for mentoring and further training in dentistry.