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What You'll Do as Head of Operations:

  • Own the three numbers (LTV/CAC, gross margin, growth) and hit targets with healthy unit economics.
  • Run clinical ops, RCM, sales, growth, quality, compliance, finance, and HR through scorecards and reviews.
  • Own the patient funnel end-to-end, from first contact through retention, and close conversion gaps.

You're a Fit If You…:

  • Have 7+ years in operations at a telehealth or tech-enabled care company and have led function leaders.
  • Have directly owned a patient funnel and contact center operations with staffing models and QA.
  • Are deeply data driven, AI native, and thrive in high-ambiguity, high-velocity environments.

Why Join Us:

  • Tackle a $25B+ healthcare navigation gap with a model investors and payers already believe in.
  • Own the operating engine of a Series A company scaling toward B, with direct work with founders.
  • Competitive salary and high equity in a fast-growing remote company with a mission to democratize healthcare navigation.

Dearest Care

Dearest Care mixes smart software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. They are a Series A company backed by top-tier investors, operating with a lean, impact-driven mindset and principles of conscious leadership.

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