Hi, I’m Will Dempsey.
Will Dempsey is a queer, neurodivergent person, a social worker, a drag queen, a dog dad, and a group practice owner of Heads Held High Counseling, with hands-on experience managing millions of dollars in claims across multiple states. Self-taught, Will is a living example that medical billing can be easily taught, no matter your learning style, and should be straightforward and accessible - especially for those looking to avoid the high costs of traditional billing services.
Will is also a vocal advocate for challenging big venture-backed behavioral health tech companies like Alma or Headway. These platforms face scrutiny over privacy and business practices. For example, Headway is currently involved in a class-action lawsuit alleging unauthorized sharing of user data, a claim the company disputes and that remains unresolved in court. Alma, meanwhile, has secured major funding from investors like Cigna Ventures and Optum Ventures to grow its insurance and practice management services.
For Will, these facts underscore the importance of carefully researching third-party service providers, considering their regulatory, legal, and operational track records before deciding to work with them. That’s why he created Heads Held High Billing as a social justice project - to educate providers not only about billing but also about the impact of the businesses they choose to support. Heads Held High Billing isn’t just a business venutre; it’s about making meaningful change.
