Chief Clinical Strategy Officer

At Two Bear Capital we believe in partnering with our portfolio companies to build the best early stage companies as possible. We look forward to working with you for Rainfall Health as their new Chief Clinical Strategy Officer/Chief Medical Officer .

Chief Medical Officer

Remote / Hybrid San Francisco• Full-Time • Executive Leadership

*please note that this role requires relocation or residency in the greater Bay Area*

About Rainfall Health

Rainfall Health (Bettermeant Inc.) is a commercial-stage health technology company on a mission to become the leading technology partner for value-based care. Backed by a $15M Series A led by Two Bear Capital, we are a fast-growing team of ~10 building solutions that help hospitals and health systems succeed under emerging risk-based payment models.

Our flagship SaaS platform enables health systems to track post-discharge patient compliance with care plans in real time — helping mandated providers avoid penalties and capture incentives under CMS’s Transforming Episode Accountability Model (TEAM) and similar value-based care mandates.

We are a Delaware C-Corp with a remote-first culture and a shared belief that technology, done right, can fundamentally improve how care is delivered and paid for in America.

The Role

As Chief Medical Officer, you will serve as the clinical and strategic voice of Rainfall Health — shaping our product vision, guiding our roadmap, and positioning the company as a trusted thought leader in value-based care. This is a senior executive role that bridges clinical expertise, health system operations, and technology strategy.

The ideal candidate brings deep experience working within or alongside health systems, a nuanced understanding of value-based care models (particularly CMS mandates such as TEAM, BPCI-A, or ACO REACH), and a passion for building products that address real clinical and operational pain points. You will work closely with the CEO, product, and commercial teams to ensure that every aspect of our offering is grounded in clinical relevance and health system reality.

Key Responsibilities

Clinical Strategy & Thought Leadership

• Serve as Rainfall Health’s primary clinical authority and external spokesperson on value-based care, care coordination, and post-acute outcomes.
• Develop and execute a thought leadership strategy — including publications, conference presentations, advisory engagements, and media — that elevates the company’s profile among health system executives and clinical leaders.
• Represent Rainfall Health at industry forums, CMS/CMMI stakeholder engagements, and payer/provider convenings.
• Monitor the evolving policy and regulatory landscape (e.g., CMS TEAM mandate, BPCI-A successors, ACO REACH) and advise leadership on strategic implications.

Product Strategy & Roadmap

• Partner with the product and engineering teams to define and prioritize the clinical product roadmap, ensuring features reflect the real-world workflow needs of health systems.
• Translate complex clinical, regulatory, and operational challenges into clear product requirements and opportunities.
• Lead clinical validation of new features and use cases, including design of pilot programs, outcomes measurement frameworks, and evidence-generation strategies.
• Identify adjacent market opportunities — including new care episodes, patient populations, or mandated programs — and shape the product strategy to capture them.
• Advise on data strategy, including clinical data integration (EHR/ADT/claims), risk stratification models, and care gap identification.

Commercial & Customer Success

• Engage directly with prospective and existing health system customers as a trusted clinical peer, supporting enterprise sales cycles and executive-level relationships.
• Serve as a key voice in customer discovery — deeply understanding the clinical and operational challenges of health system partners to inform product development.
• Partner with the commercial team to develop clinical content for proposals, RFP responses, and customer presentations.
• Support customer implementation and success by providing clinical expertise and guidance to health system care coordination and quality teams.

Organizational Leadership

• Serve as a member of the executive leadership team, contributing to company strategy, culture, and growth planning.
• Build and mentor a clinical team as the company scales, including clinical advisors, informatics staff, and care coordination experts.
• Establish clinical governance frameworks, including evidence review processes, quality standards, and outcomes reporting.
• Support fundraising efforts by articulating the clinical and market opportunity to investors and strategic partners.

Qualifications

Required

• MD, DO, RN, PA or equivalent clinical degree; active or inactive medical licensure acceptable.
• Clinical training and/or practice experience in a field directly relevant to post-acute care, care transitions, or complex care management (e.g., internal medicine, hospitalist medicine, geriatrics, cardiology, orthopedics, or related specialty).
• Demonstrated experience working within or in close partnership with health systems, integrated delivery networks, or large physician organizations.
• Deep understanding of value-based care models, particularly CMS bundled payment programs (BPCI-A, TEAM), ACO structures, or shared savings arrangements.
• Experience influencing product, technology, or operational strategy — not just clinical care delivery — in a health tech, digital health, or health system innovation context.
• Exceptional communication skills; ability to engage credibly with both clinical audiences (CMOs, physician leaders, care coordinators) and executive/board-level stakeholders (CFOs, CEOs, health system leadership).
• Comfortable operating in a fast-paced startup environment with a high degree of ambiguity and autonomy.

Preferred

• Advanced degree in health administration, public health, business, or health informatics (MHA, MPH, MBA, or equivalent).
• Prior experience as a CMO, VP of Medical Affairs, Chief Quality Officer, or equivalent senior clinical leadership role.
• Hands-on experience in care coordination program design, post-discharge follow-up workflows, or transitional care management.
• Familiarity with EHR platforms (Epic, Cerner/Oracle Health), ADT data feeds, and clinical data integration.
• Experience with clinical analytics, outcomes measurement, or population health management platforms.
• Track record of published research, policy commentary, or recognized thought leadership in value-based care, care transitions, or healthcare quality.
• Experience supporting enterprise SaaS sales cycles in a clinical or medical affairs capacity.
• Network within health system C-suites, population health programs, or post-acute care ecosystems.

What We Offer

• Executive-level compensation including base salary, performance bonus, and meaningful equity in a well-funded, high-growth company.
• The opportunity to define and lead the clinical strategy of a company at the forefront of value-based care technology.
• A collaborative, mission-driven team that moves quickly and values clinical and operational expertise equally.
• Remote-first flexibility with opportunities for in-person collaboration and customer engagement.
• Direct access to and partnership with the founding team and investors.
• A platform to become a recognized voice in the value-based care space through thought leadership, speaking, and publication.

How to Apply

Please submit your CV and a brief cover note describing your experience with value-based care models and your vision for how technology can improve care transitions and post-discharge outcomes. We welcome candidates from clinical practice, health system leadership, and health technology backgrounds.