Director of Clinical Operations

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

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.

About Dearest Care

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

What You’ll Do

Champion Scalable, High-Quality Care

• 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 numerator, denominator, exclusions, and source of truth
• Implement 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 and Develop 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, ensuring advocates spend their time with patients
• 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
• Turn recurring quality failures into product requirements, with 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 reimbursable programs, partnering with RCM on clean claims
• Maintain HIPAA and patient-privacy practices, and partner with the 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
• 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
• You are becoming AI native. 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
• Thrive in high-ambiguity, high-velocity environments and know how to prioritize
• 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 revenue 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.

• Distributed culture, mainly working out of the Americas timezone
• Commitment to diversity in thinking, in hiring, and in how we tackle problems
• Operate with excellence for our clients and building great products

Our Values:

• Conscious Leadership Values: 15 commitments to conscious leadership
• Human connection: We’re bringing healthy human relating into the world as a healing modality
• 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