[Hiring] Director of Clinical Operations @Dearest Care

Role Description

Lead the clinical team dedicated to providing exceptional patient care, ensuring measurable, visible, and continually improving quality month over month.

• Location: Remote
• Type: Full-time, hands-on leader and doer in the age of AI
• Compensation: Competitive salary + high equity

Dearest Care is growing rapidly, and sustainable growth requires every patient to receive an exceptional experience. We’re seeking a hands-on clinical operations leader to oversee our clinical team and own the quality of care delivered. Reporting to the VP of Operations, you will manage the core operation where our mission is realized—advocates, nurses, and care coordination—measured against standards you define.

This isn’t a distant management role. You will listen to calls, analyze data, write rubrics, and collaborate directly with advocates when team metrics change. You'll be instrumental in developing systems, workflows, and AI tools that make top-tier care the standard.

Qualifications

• 5+ years in clinical operations, care delivery, or healthcare quality, including 3+ years leading managers or team leads.
• Direct experience managing high-volume care operations (staffing, caseloads, service levels, QA programs).
• Proven ability to build quality or performance-management systems from scratch (standards, rubrics, calibration, escalation).
• Proficient with SQL (or equivalent) and BI tools such as Metabase—comfortable working with complex datasets.
• Eager to embrace and help shape AI-driven operational improvements.
• Knowledgeable about HIPAA and clinical documentation, with strong, concise writing skills.
• Thrive in fast-paced, high-ambiguity environments and adept at prioritization.
• Able to communicate clearly with diverse stakeholders, from senior patients to clinicians and engineers.

Requirements

• Own quality end-to-end, defining a 10-star patient experience as your north star.
• Set and maintain clear quality and patient-experience metrics, including structure, measurement, and data sources.
• Implement continuous quality monitoring across all clinical roles, sharing weekly findings and recommendations.
• Establish and refine rubrics, examples, and calibration processes so feedback is consistent.
• Guide advocates, nurses, and care coordinators through their team leads: hiring, onboarding, performance management, and professional growth.
• Manage staffing models, caseloads, service levels, and productivity to maximize patient-facing time.
• Oversee the operating cadence: weekly scorecards, monthly reviews, and quarterly target setting—ensuring every lead owns their metrics.
• Partner with Product and Engineering to embed standards and guidelines directly into workflows, making quality automatic.
• Translate recurring quality issues into actionable product requirements, with supporting evidence.
• Drive the adoption of AI tools (for call QA, summarization, documentation, follow-ups) and measure their effect on quality and efficiency.
• Develop, document, and enforce SOPs to standardize care delivery.
• Oversee all clinical documentation, care plans, consent, and time-tracking for reimbursable programs, collaborating with RCM.
• Ensure HIPAA compliance and partner with the Medical Director on escalation protocols and clinical judgment standards.
• Monitor and manage patient interactions to prevent dropped calls, delays, or missed handoffs.
• Design seamless handoffs between advocates, nurses, and physicians to ensure continuity of care.
• Instrument and report clinical quality KPIs consistently across all systems.
• Deliver insights that inform operational strategy and product development, shaping the narrative for leadership and the board.

Benefits

• Address a $25B+ healthcare navigation gap with a model trusted by investors and payers.
• Join a patient-first mission to ensure no senior navigates healthcare alone.
• Take ownership of the operation where our mission is delivered, and help shape how AI and product drive care.
• Build out high-quality care, critical to winning trust and future payer contracts.

Company Description

Dearest Care sprang from years of firsthand experience fighting for family members within the healthcare system. Our vision: everyone deserves a dedicated advocate in their healthcare journey. We combine innovative software with compassionate human advocates to help Medicare patients navigate diagnoses, bills, and care plans. Supported by investors from Omada, Oscar, and UnitedHealthcare, we’re proud of our mission-driven, agile team.

• Founded by seasoned entrepreneurs with proven success and a network of advisors spanning healthcare and technology.
• Series A company, backed by world-class investors and advisors (from Rula, Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates).
• Fast-moving, impact-driven culture focused on results, rapid iteration, and conscious leadership.