Chief of Staff

Medicaid is America’s most complex health insurer, serving some of the country’s highest‑need populations, and frontline teams are poorly equipped to navigate its complexity. The result is lower quality of care, wasted resources, and burnt out teams. We are building Rockland, an AI‑native, MSO‑lite platform to solve these problems by helping Medicaid‑serving providers automate workflows, recover lost revenue, and improve quality of care.

Founder & CEO Bennett Hauser brings deep early‑stage operating and founding experience, with a passion for building products that simplify complex workflows. Rockland was formed in partnership with founding board members Sander Duncan – a seasoned healthcare investor and operator – and Alex Tonelli, co‑founder of Funding Circle (IPO) and first investor in Collective Medical (major sale).

About The Role

We seek a highly driven Chief of Staff to work directly with Bennett to amplify the impact of Rockland’s leadership team. You’ll serve as a strategic right hand, enabling the CEO to focus on high‑priority initiatives and ensuring the rest of the company moves forward with clarity and alignment. This role is intended to be a stepping stone into future senior leadership positions such as COO or GM. You will :

Manage and prioritize cross‑functional initiatives, ensuring timely follow‑through and alignment across the company

Act as a force multiplier for the CEO – handling key communications, preparing materials, and facilitating decision‑making

Support strategic projects in product, business development, fundraising, and partnerships

Drive operational excellence by improving systems, processes, and team coordination

Serve as a trusted sounding board for the org, providing research, analysis, and perspective

Step into gaps as needed – from preparing investor decks to coordinating customer pilots

About You

This is a high‑leverage role for someone who thrives in fast‑paced, ambiguous environments and enjoys switching between strategy, operations, and execution. You’re a natural problem‑solver with excellent judgment, and energized by wearing many hats in an early‑stage environment. You have :

Minimum 5–8 years of experience in consulting, strategy, operations, or chief of staff roles (healthcare or tech background a plus)

Exceptional project management skills with a track record of delivering results across multiple workstreams

Strong written and verbal communication skills, with the ability to synthesize complex ideas clearly

High emotional intelligence, discretion, and the ability to earn trust quickly

Comfort working in a fast‑paced startup environment with shifting priorities

Located in or willing to relocate to San Francisco; we believe early‑stage is best done in person

Referrals increase your chances of interviewing at Rockland by 2x

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