Chief Operating Officer

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.

What Success Looks Like in 12 Months

• Significantly improving GM with AI workflows running on all aspects of the business

• All provider credentialing and payer contracts are up-to-date and tracked in a clean, automated system.

• Leadership spends more time on strategy because you’ve taken operational firefighting off their plate.

Why Join Us

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

• Our team is patient first and on a mission to make sure seniors don't have to navigate their healthcare alone.

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

• This is not a “corporate healthcare” role—your work 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 (4x’d rev in less than 6 months)

• Remote: leadership team meets in San Francisco 1-2x per month

• Ownership: Partner with the CEO as a peer on company direction

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 commitment 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.