We’re a small team with big ideas and a passion for doing things well.
Meet Will (he/him)
Founder & Practice Consultant
Will Dempsey, LICSW, is the founder of Heads Held High Billing and owner of Heads Held High Counseling, an insurance-based group therapy practice. His background as both a clinician and practice owner shapes his work with therapists and group practice owners navigating billing, growth, and business operations. Will’s approach is direct, practical, and nonjudgmental, with a focus on helping providers understand the “why” behind their options rather than prescribing one right way to run a practice. As a neurodivergent clinician and business owner, he values clear, accessible systems and brings queer-affirming and anti-racist values to his work. Outside of work, he enjoys musical theater and live reality games.
Meet Zak (he/him)
Billing specialist & Educator
Zak Pekovic is a Billing Specialist & Educator with Heads Held High Billing, supporting behavioral health providers with billing, credentialing, claims follow-up, and insurance navigation. He previously managed billing for Heads Held High Counseling, giving him firsthand experience with the day-to-day demands of an active insurance-based group practice. Known for being detail-oriented, organized, and clear in his communication, Zak also develops and leads HHHB’s group billing trainings, helping clinicians better understand the systems behind their claims and reimbursement. A Chicago native, he enjoys running and spending time at the beach.
