[Hiring] Head of Operations @Dearest Care

Role Description

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
• HR

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. 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.

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.
• Expand gross margin month after month.
• Hit our growth targets: Pipeline, conversion, activation, retention.
• Run the Operating Engine: clinical ops, RCM, sales, growth, quality, compliance, finance and HR.
• Own the Patient Funnel: journey from first contact through onboarding, ongoing engagement, and retention.
• Build a World Class Advocate Operation: capacity, staffing models, service levels, productivity, QA.
• Build AI Native Operations: partner with tech and product team to drive AI into the operation.
• Champion the Patient Experience: monitor the moments that matter and close the loop on issues.

Qualifications

• 7+ years in operations at a telehealth, tech enabled care, or consumer healthtech company.
• Experience owning a patient funnel directly.
• Experience running contact center or high volume care operations.
• Experience with RCM, credentialing, or payer enrollment directly.
• Deeply data driven.
• Thrive in high ambiguity, high velocity environments.
• Desire to own the whole engine, not just a lane.
• Clear communication skills.

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.
• Gross margin has improved materially.
• Key operational areas run through clean systems instead of heroics and firefighting.
• Your scope has grown, because the numbers earned it.

Why Join Us

• Tackling a $25B+ healthcare navigation gap.
• Own the operating engine of a Series A company scaling toward B.
• Work directly with founders, influencing product and market strategies.
• Execution will directly impact major contracts in the next 12 months.

The Package

• Competitive salary + high equity.
• Remote: leadership team meets periodically in SF/Bay Area.
• Real autonomy over how the operating engine runs.

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.

• Distributed culture, mainly working out of the Americas timezone.
• Diverse in thinking, hiring, and problem-solving.
• Prioritize excellent operations for clients.

Conscious Leadership Values

• Human connection.
• Playful creativity.
• Excellence in execution.
• Stop the ego.
• Outwork smartly, competitive for our customers.

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.