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Rick Workman

Founder and Executive Chairman at Heartland Dental

Windermere, Florida

RW
Why they matter

Founded and scaled the DSO rollup model that defined dental private equity, giving unmatched insight into consolidation playbooks, doctor alignment, and what breaks post-scale.

Background

Dr. Rick Workman is a practicing dentist who founded Heartland Dental in 1997 in Effingham, Illinois, after selling his own 29-office practice for $15.8 million. He built Heartland into the largest dental support organization (DSO) in the U.S. — now 1,900+ supported practices across 39 states with $3.6B in 2024 revenue — pioneering the DSO rollup model that private equity later poured billions into. He remains Founder and Executive Chairman and has since become a healthcare-focused PE advisor and sports team investor.

Notable deals

  • 2012
    Sold majority interest in Heartland Dental to Ontario Teachers' Pension Plan (Teachers' Private Capital), valuing the company at ~$1.3B
  • 2018
    KKR acquired majority (58%) interest in Heartland Dental from Ontario Teachers' at a $2.8B valuation; Workman retained a significant stake as Executive Chairman
  • 2025
    Left the Orlando Dreamers MLB expansion bid (where he was anchor investor) to join Patrick Zalupski's ownership group acquiring the Tampa Bay Rays

Call-prep brief

Rick Workman — Founder & Executive Chairman, Heartland Dental

Background

  • Practicing dentist turned founder; built Heartland Dental from a single Effingham, IL office (1997) into the largest U.S. dental support organization (1,900+ practices, 39 states, ~$3.6B revenue in 2024).
  • Took the company through two majority PE recapitalizations: Ontario Teachers' Pension Plan (2012, ~$1.3B) then KKR (2018, ~$2.8B), retaining equity and the Executive Chairman seat through both.

Current focus

  • Still Active Executive Chairman at Heartland; also Chair of the Executive Advisor Team at New Harbor Capital, a healthcare-focused lower-middle-market PE firm, advising portfolio companies like Premier ENT & Allergy and formerly PT Solutions.
  • Increasingly active outside dentistry: became a minority owner in the group that acquired the Tampa Bay Rays (Sept 2025) after being an anchor investor in the rival Orlando Dreamers MLB expansion push.

What he cares about

  • The "doctor-led" DSO model — preserving clinical autonomy while centralizing non-clinical support/back-office functions; is vocal about avoiding over-corporatization of dental practice.
  • Physician/dentist-alignment mechanics in rollups: equity retention, culture, and growth-stage governance as DSOs pass through multiple PE ownership cycles.

Sensitivities

  • His abrupt switch from the Orlando Dreamers to the Rays ownership group surprised former partners — worth reading the room before raising it directly.
  • As a healthcare-adjacent operator now moonlighting in sports ownership, he may be less available/attentive to new dental-sector outreach.

Questions to ask

  1. What structural terms (equity retention, board rights, governance) made the OTPP-to-KKR transition work for doctors and founders — and what would you change?
  2. Where does the DSO rollup model break down as consolidators chase scale — clinical quality, doctor retention, or regulatory scrutiny?
  3. What is New Harbor Capital's thesis for healthcare-services rollups outside dental (ENT, physical therapy), and how transferable is the Heartland playbook?

Outreach draft

Subject
Insights on dental DSO rollup economics
Dr. Workman, I'm reaching out from [FIRM], where we're evaluating a physician/dental practice rollup opportunity and studying how DSO consolidators scale without eroding clinical quality or doctor buy-in. Given your work building Heartland Dental through two major PE recapitalizations, and your current advisory role at New Harbor Capital, your perspective on governance, doctor alignment, and growth-stage pitfalls would be invaluable. Would you have 20-30 minutes for a call in the next couple of weeks? Happy to work around your schedule and compensate for your time per standard expert-network terms. Thank you for considering, [Placeholder Name]

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