Chief Operating Officer

Job description

Build the systems that let us scale care without losing the human touch.

📍 Location: Remote, leadership team meets in San Francisco 1-2x per month

💼 Type: Full-time — hands-on, not a manager role per say, doer in the age of AI

💰 Comp: Competitive salary + high equity

Why This Role Exists

Dearest Care is growing fast — but growth only works if the patient and customer experience stays exceptional and we have the operational backbone to deliver consistently. We’re looking for a senior, hands-on operator who can work across finance, strategy, credentialing + payer contracting, and day-to-day ops while keeping a sharp eye on patient experience and quality. You’ll own the connective tissue between our advocates, payers, and leadership team — ensuring no patient falls through the cracks, no credentialing deadline slips, and no operational ball is dropped.

This is not a “manage people from a distance” role. You’ll roll up your sleeves, fix broken workflows yourself, and bring back lessons 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 COO

Gross Margin that will help us scale to being a unicorn

Completely own end to end on this number and drive efficiency and run operations for the company as a whole

Manage provider credentialing, payer enrollment, and ongoing compliance.

Keep every contract, license, and NPI file audit-ready.

Be the Operational Glue and drive the company

Run Clinical Ops, RCM, Customer Success, Finance, Compliance— > Provide product insights based on the operational insights.

Coordinate across advocates, providers, and payers to resolve bottlenecks fast.

Set operational priorities in lockstep with the founding team.

Drive Process Excellence

Build and document repeatable workflows for billing, scheduling, and intake.

Spot operational inefficiencies and fix them — quickly.

Champion the Customer Experience

Monitor patient and partner touch points to ensure a high-quality, consistent experience.

Close the loop on dropped calls, delayed follow-ups, or missed handoffs.

Own the Data & Insights Narrative

Track KPIs across credentialing, throughput, and patient satisfaction.

Drive investor-facing reporting and board-level operational narratives.

You’re a Fit If You…

Have 7+ years in healthcare operations at a startup, clinic, or provider network.

You are becoming AI native. Period. Old school thinking isn’t going to work here.

You are data-driven, can size and be brutally honest on when things break and fix them.

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

Thrive in high-ambiguity, high-velocity environments and know how to prioritize.

Are hands-on and execution-driven — you solve problems directly, then build the process to prevent them. This is not a 9 to 5 role.

Communicate clearly with diverse stakeholders — from an anxious senior patient to a health plan contracting lead.

Bonus points if you’ve

Worked with Medicare or Medicaid populations.

Taking a company from seed to series C

Been the “right hand” to a founder or exec team in a high-growth healthcare company.