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.
• Own the Quality Narrative
• Own instrumentation and reporting of clinical and quality KPIs across every system of record.
• Surface insights to Ops and Product that shape the roadmap and our operational story for leadership and the board.

You’re a Fit If You…

• Have 5+ years in clinical operations, care delivery, or healthcare quality, including 3+ years leading managers or team leads.
• Have run a high-volume care operation yourself: staffing models, caseloads, service levels, and a closed-loop QA program. You can say what broke at 3x volume.
• Have built a quality or performance-management system from scratch: documented standards, rubrics, calibration, and an escalation path.
• Are hands-on with data. You write your own SQL or equivalent and work fluently in BI tools like Metabase. We’ll test this with a real, messy dataset.
• You are becoming AI native. Period. Old school thinking isn’t going to work here.
• Have partnered with product or engineering to fix an operational problem in the product, not around it.
• Know HIPAA and clinical documentation requirements, and write well and briefly. You can produce a one-page rubric with no adjectives in it.
• Thrive in high-ambiguity, high-velocity environments and know how to prioritize. This is not a 9 to 5 role.
• Communicate clearly with diverse stakeholders, from an anxious senior patient to a physician to an engineer.

Bonus points if you’ve:

• Held an RN or other clinical license, or worked in care coordination, care management, or patient navigation.
• Worked with Medicare or Medicare Advantage populations, or programs like CCM, PIN, or BHI.
• Worked at a Series A–C telehealth or tech-enabled care company.
• Run care-team or contact-center operations for older adults.

What Success Looks Like in 12 Months

• Every clinical role is measured against a stable, documented quality standard, and leadership trusts the weekly quality report.
• Patient experience (show-up, NPS, engagement) has measurably improved, with clear attribution to your changes.
• Quality is enforced by the workflow itself across meaningful parts of the operation, with AI running call QA, documentation, and follow-up.
• The clinical team has scaled without quality slipping, led by team leads you hired or developed.
• The clinical operation is audit-ready on any given day.

Why Join Us

• We’re tackling a $25B+ healthcare navigation gap with a model investors and payers already believe in.
• Our team is patient first and on a mission to make sure seniors don't have to navigate their healthcare alone.
• You’ll own the operation where our mission happens, and shape how product and AI are built into the care we deliver.
• This is not a “corporate healthcare” role—the quality of care you build is what earns patient trust and wins our next payer contracts.

The Package

• Competitive salary + high equity as we’re scaling significantly fast (4x’d rev in less than 6 months)
• Remote: leadership team meets in San Francisco 1-2x per month
• Ownership: the clinical operation and its quality are yours, with the decision rights to run them

Our Vision + Culture:

We envision a future where every American has access to a personal healthcare navigator. Our platform is designed to democratize healthcare navigation, offering tools and resources that were previously unavailable to many. By addressing the challenges faced by patient advocates and those navigating chronic diseases or healthcare illiteracy, we're paving the way for a more inclusive and accessible healthcare system.

We have a distributed culture, mainly working out of the Americas timezone. We strive to be diverse in thinking, in hiring, and in how we tackle problems. We believe that operating excellently for our clients is our number one priority and building great products is critical.

Our Values:

• 15 commitments to conscious leadership
• Human connection: We’re bringing healthy human relating into the world as a healing modality, and we prioritize healthy relating within our team and in everything we do.
• Playful creativity: We bring levity, fun, and playfulness to our work.
• Excellence: in executing, thinking, writing, and communicating.
• Stop the ego: hard conversations and ripping the bandaid earlier than later. Uplift each other.
• Outwork smartly, competitive for our customers: Impact is driven that's measured on driving benefit to the end customer.

Our story: https://vimeo.com/1188185714

Dearest Care is an equal opportunity employer committed to diversity and inclusion. We welcome applications from all qualified individuals, regardless of their background. Join us in transforming healthcare navigation.