Director, Clinical Quality

Dearest Care was founded after years of fighting the system on behalf of our own founders' families. Our vision is simple: every patient deserves a relentless advocate. Today, we combine smart software and human advocacy to guide Medicare patients through diagnoses, medical bills, and care plans. Our mission has resonated with investors from Omada, Oscar, and UnitedHealthcare, and we’re proud of the driven team we’ve built.

Founded by serial entrepreneurs with successful exits and supported by a deep bench of advisors in healthcare and tech, we’re a Series A company backed by top-tier investors and leaders from Rula, Oscar Health, Omada, Galileo, One Medical, Ro, United, Uber, and Postmates.

We move fast, execute with purpose, and operate with a lean, impact-focused mindset. Our principles are rooted in conscious leadership, a commitment to getting things done, and a focus on achieving meaningful results through rapid iteration and execution.

As the Director of Clinical Quality at Dearest Care, you will own the measurement and management of care quality across the organization. You will define standards, build and instrument measurement systems, run a tight monitoring cadence, and partner with Product and Tech to embed quality directly into workflows—eliminating reliance on retroactive inspection.

This is a hands-on role: you will extract data, develop rubrics, and deliver reports yourself. While strategy sits with the Head of Clinical Operations, you will create and operate the system that makes quality and outcomes measurable. You’ll also be the key voice interpreting what the numbers truly reveal.

• Own all aspects of quality measurement, with a focus on delivering a standout patient experience

• Instrument, measure, and report on metrics across all relevant systems

• Develop, document, and implement SOPs to standardize quality processes across teams

• Surface insights from data analytics to inform operational and product roadmaps

• Run continuous quality monitoring for all roles within Clinical Operations

• Report weekly findings to leadership with clear recommendations for improvement

• Own the coaching framework: create rubrics, examples, and calibration processes to deliver consistent feedback

• Collaborate with the Head of Clinical Operations to integrate quality standards into hiring, onboarding, training, and statements of work

• Partner with Product and Tech to embed quality directly into clinical and operational workflows

• Document recurring quality issues and create clear product requirements, with data-backed evidence for the roadmap

To ensure clarity of responsibilities, this role does not own:

• Compliance or outcomes strategy (owned by Head of Clinical Operations)

• Direct delivery of training or coaching (owned by trainers and team leads)

• People management at hire (headcount comes after the system is running)

• Clinical judgment (handled by clinical leadership; this role covers administrative/service obligations)

• Bachelor’s degree or equivalent practical experience in analytical operations

• 5+ years in consulting, healthcare quality operations, or ops analytics, including 2+ years owning a metric at the leadership level

• Strong, hands-on analytical skills (SQL, BI tools like Metabase, and data modeling)

• Experience rigorously defining and defending metrics (numerators, denominators, exclusions, sources of truth)

• Prior experience building or running a documented performance management or QA process

• Evidence of effective partnership with product or engineering to address operational issues at their root

• Clear, concise writing skills – able to produce a one-page rubric with no adjectives

• Working knowledge of HIPAA and patient data privacy standards

• Experience in healthcare services, care coordination, patient navigation, or payer operations

• Familiarity with Medicare or Medicare Advantage

• Early-stage or startup experience (Series A/B)

• Proficient in AI tools to maximize the leverage of a lean team

• Experience mentoring or coaching analysts or managing small teams (growth potential for this role)

• Competitive salary and high equity as we rapidly scale

• Remote position

• Ownership of quality across the clinical team, reporting to the Head of Clinical Operations

Our vision is to ensure every American has access to a personal healthcare navigator. We aim to democratize healthcare navigation with tools and resources that were previously out of reach for many. By supporting advocates and patients facing chronic disease or healthcare illiteracy, we are building a more inclusive, accessible system.

We operate as a distributed team (primarily in the Americas time zone), value diversity in our people and perspectives, and believe operational excellence for clients and great product building go hand-in-hand.

• Conscious leadership: We practice all 15 commitments

• Human connection: Both internally and in our care model

• Playful creativity: We believe fun and innovation go together

• Excellence: In execution, thinking, writing, and communication

• Ego-free feedback: Direct conversations and uplifting the team

• Smart, competitive work: Impact is measured by benefit to our customers

Watch our story

Dearest Care is an equal opportunity employer committed to diversity and inclusion. We welcome applicants from all backgrounds. Join us in transforming healthcare navigation.