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

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.

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 United Healthcare 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.

• 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 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 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.

• 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.

• Partner with our tech and product team to…