Director of Clinical Operations

Director of Clinical Operations — Job Description

Lead the team that cares for our patients, and make the quality of that care measurable, visible, and better every month.

📍 Location: Remote

💼 Type: Full-time: hands-on leader, doer in the age of AI

💰 Comp: Competitive salary + high equity

Why This Role Exists

Dearest Care is growing fast, and growth only works if every patient gets the same exceptional experience. We’re looking for a hands-on clinical operations leader to run our entire clinical team and own the quality of the care it delivers. You’ll report to our VP of Operations and own the operation where our mission actually happens: advocates, nurses, and care coordination, measured against standards you define.

This is not a “manage people from a distance” role. You’ll listen to calls, pull your own data, write the rubric, and sit with advocates when a number moves. Then you’ll build the systems, workflows, and AI tooling that make great care the default, not the exception.

About Dearest Care

We started Dearest Care after years of fighting the system for our own founders' families. Our vision: everyone deserves a fighter like that. Today we mix smart software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. Investors from Omada, Oscar, and UnitedHealthcare believe in the mission—and in the scrappy team we have built.

Founded by 2x and 3x time experienced entrepreneurs with successful exits, with deep roster of advisors in healthcare + tech expertise.

Series A company backed by top-tier investors and advisors, including founders and executives from Rula, Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates.

We move fast and execute with purpose, operating with a lean, impact-driven mindset. We're guided by principles of conscious leadership, a commitment to getting things done (GSD), and a focus on achieving results through hard work, rapid iteration, and swift execution.

What You’ll Do as Director of Clinical Operations

Quality of care that lets us scale without losing the human touch

Own quality end to end, with a 10-star patient experience as the north star.

Define our quality and patient-experience metrics down to numerator, denominator, exclusions, and source of truth, and hold them steady under pressure.

Run continuous quality monitoring for every clinical role, with weekly findings and recommendations to leadership.

Own the coaching system: rubrics, worked examples, and calibration so feedback is consistent no matter who delivers it.

Lead the Clinical Team

Lead advocates, nurses, and care coordinators through their team leads: hiring, onboarding, performance management, and growth.

Own capacity, staffing models, caseloads, service levels, and productivity, so advocates spend their time with patients, not fighting internal processes.

Run the clinical operating cadence: weekly scorecard, monthly review with the VP of Operations, quarterly targets. Every lead knows their number.

Build Quality Into the Product

Partner with Product and Engineering to embed standards directly into patient and advocate workflows, so the system enforces them rather than after-the-fact review.

Turn recurring quality failures into product requirements, with the evidence attached.

Drive AI into clinical operations (call QA, summarization, documentation, follow-up) and measure the impact on quality, capacity, and cost.

Keep the Operation Audit-Ready

Write, document, and enforce the SOPs that standardize how care is delivered.

Own clinical documentation, care plans, consent, and time-tracking requirements behind our reimbursable programs, partnering with RCM on clean claims.

Maintain HIPAA and patient-privacy practices, and partner with our Medical Director on escalation and clinical-judgment protocols.

Champion the Patient Experience

Monitor patient touch points and close the loop on dropped calls, delayed follow-ups, and missed handoffs.

Design the handoffs between advocates, nurses, and physicians so no patient falls through the cracks.