Head of Operations

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

📍 Location: Remote

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

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

Why This Role Exists

Dearest Care is growing fast. We just raised a Series A and the constraint on our next chapter is not demand. It is operational horsepower.

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.

As the Head of Ops you will be tasked with running the operational execution arm for the company. The myriad functions, the metrics, and the operating cadence are yours to run, with the autonomy to run them your way.

This is not a manage from a distance role. You'll listen to calls, walk the funnel yourself, fix broken workflows, deploy AI, and turn what you learn into systems that make us faster, cleaner, and more scalable.

A bit 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 Head of Operations

Own the Three Numbers (LTV/CAC, Gross Margin and Growth)

• 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.

• Expand gross margin month after month. Find the leaks across the funnel, care delivery, and RCM, then close them.

• Hit our growth targets. Pipeline, conversion, activation, retention. The numbers land, or the founders hear it from you first with a plan attached.

Run the Operating Engine

• 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. Everyone knows their number.

• When something breaks, get to the root cause fast, fix it, and build the process so it does not happen again.

Own the Patient Funnel

• Own the journey from first contact through onboarding, first physician and advocate encounter, ongoing engagement, and retention. Know the conversion rates cold and where patients are falling out.

• 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

• Own capacity, staffing models, service levels, productivity, QA, and the systems our advocates use every day.

• 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.

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

Champion the Patient Experience

• Monitor the moments that matter and close the loop on dropped calls, missed handoffs, delayed follow ups, and unresolved issues.

• These are anxious seniors, not tickets. Nothing falls through the cracks on your watch.

You're a Fit If You…

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

• Have owned a patient funnel directly. You can whiteboard your last one from memory, stage by stage, with the conversion rates you inherited and the ones you left behind.

• 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 becoming AI native. Period. Old school thinking isn't going to work here.

• You are deeply data driven. You know your numbers, can identify when something is breaking, and move quickly to fix it.

• Thrive in high ambiguity, high velocity environments and prioritize ruthlessly. This is not a 9 to 5 role.

• Want the whole engine, not a lane. You know the difference between a big mandate and a big title, and you're here for the mandate.

• Communicate clearly with everyone from an anxious senior patient to a health plan contracting lead.

Bonus points if you've:

• Worked with Medicare or Medicaid populations.

• Worked in an early stage company from Series A toward Series C.

• Run contact center operations for a senior population.

• Worked closely with founders or exec team in a high growth healthcare company.

What Success Looks Like in 12 Months

• 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.

• Your scope has grown, because the numbers earned it.

Why Join Us

• We're tackling a $25B+ healthcare navigation gap with a model investors and payers already believe in.

• You'll own the operating engine of a Series A company scaling toward B. Most operators wait a decade for this mandate.

• You'll work directly with founders, influencing product, go to market, and Series B readiness.

• This is not a corporate healthcare role. Your execution will directly decide if we win major contracts in the next 12 months.

The Package

• Competitive salary + high equity as we're scaling significantly fast
  Remote: leadership team meets periodically in SF/Bay Area

• Ownership: the operating engine is yours, with real autonomy over how it runs and a leadership team built so that stays true

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 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.