Head of Business Operations - Remote

Build and run the engine that lets us scale care without losing the human touch.

Location: Remote, periodic travel to SF

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

Comp: Competitive salary ($225k/yr - $245/yr) + high equity

We're looking for a senior, hands-on operator to own the entire operating engine of the company: clinical ops, RCM, sales, growth, quality, compliance, finance and HR, and more broadly the patient funnel as well as the patient experience end to end. You'll own the numbers that decide whether we can scale: healthy unit economics, gross margin, and our growth targets.

This is not a manage from a distance role. Today we mix smart software with human advocates to guide Medicare patients through diagnoses, bills, and care plans. 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.

Grow with healthy unit economics. CAC, cost to serve, contribution margin, and LTV by cohort. Every patient we add makes the business stronger, not just bigger.

Pipeline, conversion, activation, retention. Run clinical ops (advocates, providers, call center ops), RCM (contracting, credentialing, claims), sales, growth, quality, compliance, finance and HR, through one operating rhythm: weekly scorecards, monthly reviews, quarterly targets. Own speed to lead, channel economics, and pipeline quality. Experiment relentlessly and turn what you learn into better operations and better product decisions.

Build a World Class Advocate Operation

Make it easier for advocates to spend their time helping patients instead of fighting internal processes.

Build AI Native Operations

Partner with our tech and product team to drive AI into the actual operation: call QA, summarization, follow up, documentation, RCM, credentialing, reporting, and other manual workflows.

AI should lower cost, increase capacity, improve quality, increase conversion, or create a better patient experience.

Have 10+ years in operations at a telehealth, tech enabled care, or consumer healthtech company, and have led function leaders, not just teams.

Have run contact center or high volume care operations yourself: staffing models, service levels, QA.

Have touched RCM, credentialing, or payer enrollment directly, not just managed someone else doing it.

You are deeply data driven. Communicate clearly with everyone from an anxious senior patient to a health plan contracting lead.

Bonus points if you've:

Run contact center operations for a senior population.

Unit economics are healthy and improving, enabling us to also hit our growth targets with every risk surfaced by you first, weeks early.

Gross margin has improved materially, with AI running across meaningful parts of the operation and clear attribution to the gains.

Key operational areas such as credentialing, contracting, claims, compliance, finance, HR, and quality control run through clean systems instead of heroics and firefighting.

Competitive salary + high equity as we're scaling significantly fast

Remote: leadership team meets periodically in SF/Bay Area

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. We believe that operating excellently for our clients is our number one priority and building great products is critical.

Outwork smartly, competitive for our customers: Impact is driven that's measured on driving benefit to the end customer.

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