Dearest Care→
Director of Clinical Operations at Dearest Care in Remote
Job Description
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.
Conscious Leadership Values: 15 commitment 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:
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.
Director of Clinical Operations
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
Why This Role Exists
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 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
Lead and Develop the Clinical Team
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
Integrate Quality with Product and Technology
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
Maintain Audit-Readiness
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
Elevate the Patient Experience
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
Own and Share the Quality Narrative
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
About You
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
Experienced partnering with product or engineering to address operational challenges at their root
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
Bonus Points If You:
Hold an RN or other clinical license, or have experience in care coordination or navigation
Have worked with Medicare, MA, CCM, PIN, or BHI programs
Have experience at an early-stage telehealth or tech-enabled care company
Managed contact-center operations or care teams for older adults
What Success Looks Like (12 Months)
Every clinical role is measured against stable, documented standards; weekly quality reports are trusted by leadership
Patient experience metrics (show rates, NPS, engagement) have measurably improved, with clear attribution to your work
Quality is seamlessly enforced by workflows and AI-driven processes
The clinical team has grown without any decline in quality, led by impactful managers you have hired or developed
The operation is audit-ready at all times
Why Join Us
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
The Package
Competitive salary + high equity (rapid growth: 4x revenue in under 6 months)
Fully remote, with leadership meetings in San Francisco 1–2x per month
Full operational ownership and decision rights
Our Vision & Culture
We believe every American should have access to a personal healthcare navigator. By democratizing healthcare navigation and supporting those who face chronic illnesses or health literacy challenges, we’re building a more inclusive system.
Distributed team primarily in the Americas time zones
Commitment to diversity in perspective, hiring, and problem-solving
Operate with excellence for clients and a product-focused approach
Our Values
15 commitments to conscious leadership
Human connection as a healing modality—in our team and patient care
Playful creativity, levity, and fun
Excellence in execution, thinking, writing, and communication
Ego-free, direct feedback and team uplift
Smart, competitive work with clear customer impact
Dearest Care is an equal opportunity employer, dedicated to diversity and inclusion. We welcome applicants from all backgrounds. Join us in transforming healthcare navigation.