Head of Operations

NYC, in-person (Mid-town).

About Leland Care

The typical US senior sees seven physicians across four practices plus insurers, pharmacies, family members, and facility staff. No one has the full picture. Fragmented data in incompatible systems leaves seniors and families managing chaos instead of focusing on living well.

Leland is building the first unified system of record for aging to help seniors live longer, healthier, and happier lives. With one complete record of a senior's health and life, AI can intelligently analyze the full picture to surface risks, gaps, and opportunities, while the senior's trusted human navigator guides the next best actions and removes friction so families can actually follow through. This turns fragmented information into proactive, coordinated support that extends healthy, independent years.

We have a multi-year funding runway and are launching pilots in 2026 with providers and already in active conversations with major US health systems. The company is led by a Stanford GSB founder with experience scaling new businesses at Sword Health and Homebase.

About the role
As the Founding Head of Operations, you are the operating backbone of the company. You turn strategy into execution and you build the machine that lets a regulated healthcare company move fast without breaking. One day you are running a special project or prepping the board, the next you are standing up our billing rails or fixing a broken process before it scales.

You will own four things:

• Force multiplier to the CEO: Run special projects end-to-end, drive hiring and onboarding, support fundraising and board prep, and own the dozens of cross-functional threads that keep the company moving.
• Compliance and billing rails: Stand up the infrastructure that makes us legitimate and reimbursable. HIPAA, BAA, OIG review, SOC 2, entity and TIN, Medicare enrollment, consent and copay workflows, and audit-ready documentation.
• Revenue cycle: Run the rails day to day. Time tracking, claims submission, acceptance, denials, and days to cash. Turn delivered navigation into clean, collected revenue.
• Analytics and reporting: Build the reporting backbone. Track outcomes and leading indicators, run the weekly cadence, and give the team and the board a clear, honest picture of what is working.

Expect to make high-leverage operational decisions, move fast, and own outcomes end-to-end with minimal process. This is a true 0-1 role. You will define how the company runs.

Who we're looking for

• You are a generalist operator who goes deep. You can run a fundraising workstream and a claims workflow in the same week and do both well.
• You have hands-on clinical billing experience. You have personally run Medicare, Medicaid, or commercial billing, documentation, credentialing, and denials, and know what breaks and how to stay compliant.
• High agency. You figure things out, move fast, and do whatever it takes to make progress. You don't wait for perfect requirements or perfect conditions.
• You thrive in ambiguity and chaos. You prefer clear goals and maximum freedom over hand-holding and process.
• You bring structure to messes. You see the broken process or the missing system before it becomes a fire, and you build the fix.
• Low ego, high output. You want the intensity and ownership that only exists at the earliest stage of a company.

If you need constant direction, clear roadmaps, or a well-defined role, this is not the right place.

Compensation and benefits

$150k-$170k salary + generous founder shares. We also provide healthcare benefits.