Head of Operations

About the role

Leland is building the first unified system of record for aging to help seniors live longer, healthier, and happier lives. The typical US senior sees seven physicians across four practices plus insurers, pharmacies, family members, and facility staff, leaving fragmented data scattered across incompatible systems. This role owns turning that chaos into a single, coherent record where AI can intelligently analyze the full picture to surface risks, gaps, and opportunities for proactive support. You will act as the force multiplier for the CEO, running special projects end-to-end while standing up the billing rails and fixing broken processes before they scale. The successful hire will build the reporting backbone that tracks outcomes and leading indicators, ensuring the team and board see an honest picture of progress. You will own the compliance and billing infrastructure that makes the company legitimate and reimbursable, from HIPAA and consent workflows to Medicare enrollment and audit-ready documentation. This is a true 0-1 role where you define how the company runs with high-leverage decisions and minimal process.

Key facts

What you'll do

Drive special projects end-to-end for the CEO while simultaneously standing up billing rails and ensuring audit-ready documentation.

Own the compliance backbone including HIPAA, BAAs, OIG review, SOC 2, entity and TIN setup, and Medicare enrollment to keep the company legitimate.

Run revenue cycle operations day in and day out, managing time tracking, claims submission, acceptance, denials, and days to cash.

Build the analytics and reporting backbone that tracks outcomes and leading indicators to guide strategic decisions.

Remove friction for families and navigators so seniors can follow through on recommended actions and stay on their path to living well.

Fix broken processes the moment they appear, using high agency to keep the machine moving without waiting for perfect conditions.

Create a single unified record of aging by integrating fragmented data from incompatible systems into a coherent, actionable view.

Support fundraising and board preparation with clean narratives, metrics, and documentation that reflect operational excellence.

Implement consent and copay workflows that balance regulatory requirements with seamless navigation experiences.

Establish the weekly cadence and reporting rhythm that aligns the team around clear outcomes and emerging risks.

Maintain strict compliance and documentation standards so that every decision is traceable and defensible to regulators and partners.

Continuously identify where processes break and design the fixes before those issues scale into larger failures.

Requirements

You must have hands-on clinical billing experience with Medicare, Medicaid, or commercial billing, documentation, credentialing, and denials.

You must understand what breaks in billing workflows and how to stay compliant while moving fast in a regulated environment.

You must be a generalist operator capable of running a fundraising workstream and a claims workflow in the same week without dropping quality.

You must thrive in ambiguity and chaos, preferring clear goals and maximum freedom over hand-holding and rigid process.

You must bring structure to messy situations by seeing missing systems and broken processes before they become fires.

You must have low ego and high output, embracing the intensity and ownership that exists only at the earliest stage of a company.

You must be able to build and manage an audit-ready documentation trail for HIPAA, SOC 2, and OIG reviews.

You must be comfortable owning outcomes end-to-end with minimal process and making high-leverage operational decisions.

Nice to have

Experience launching pilots with providers and engaging in active conversations with major US health systems.

Understanding of how AI can intelligently analyze a complete record of aging to surface risks, gaps, and opportunities.

Practical notes

This role requires significant travel within New York City and surrounding pilot sites.

Candidates must be eligible to work in the United States without sponsorship.

The engagement is full time with a multi-year funding runway supporting aggressive 2026 pilot launches.