In 1992, along with community activist David Curtis, Lippert founded the Samara Foundation of Vermont, an LGBT community foundation whose mission was "to improve the quality of life of Vermont's lesbian, gay, bisexual and transgender citizens."
For twenty years prior to serving in the Vermont legislature, Lippert worked in community mental health services, serving as a psychotherapist and substance abuse counselor, and for ten years as the Executive Director of the Counseling Service of Addison County.