Chief Technology Officer

At

Two Bear Capital

we believe in partnering with our founders and portfolio companies to build the best teams possible. We look forward to speaking with you about

Rainfall Health

and their search for the first

Chief Technology Officer

opportunity.

Chief Technology Officer

Early-Stage Health Tech \| Value-Based Care \| Hybrid (SF)

About Rainfall Health

We're a fast-growing health tech company on a mission to make care delivery smarter, faster, and more equitable. Our AI platform helps health systems and provider groups streamline clinical workflows and close care gaps. Leveraging AI to drive meaningful healthcare impact for patients.

Role Overview

The Chief Technology Officer will be a core member of the executive team and the strategic architect of our technology vision. Reporting directly to the CEO, you will own the full technology roadmap — from EHR integration infrastructure and cloud platform architecture to data security, regulatory compliance, and engineering team building.

This is a role for a seasoned technology leader who combines deep healthcare IT expertise with the entrepreneurial drive to build from the ground up. You will work closely with clinical, product, and commercial teams to ensure our platform earns the trust of hospital systems and scales to meet the demands of a rapidly evolving CMS regulatory landscape.

Key Responsibilities

Technology Strategy \& Vision

• Define and own the company's multi-year technology roadmap, aligned to value-based care market needs and CMS policy evolution
• Serve as the internal and external voice of technology — representing our platform's capabilities to hospital system IT departments, CIOs, and key stakeholders
• Make high-stakes architectural decisions balancing speed-to-market, scalability, security, and regulatory compliance

EHR Integration \& Interoperability

• Lead strategy and execution for EHR integrations (Epic, Cerner/Oracle Health, athenahealth, etc.) using HL7 FHIR, SMART on FHIR, and applicable standards
• Navigate EHR vendor certification processes, App Orchard listings, and health system IT security reviews
• Ensure the platform meets ONC interoperability requirements and CMS data exchange mandates

Platform Architecture \& Engineering

• Architect a scalable, cloud-native platform (AWS/Azure/GCP) designed for HIPAA compliance, high availability, and enterprise-grade security
• Oversee software development lifecycle including CI/CD, QA, and release management practices
• Build and scale a high-performing engineering team; establish culture, hiring practices, and performance standards

Regulatory \& Security Compliance

• Ensure all systems meet HIPAA/HITECH requirements, SOC 2 Type II standards, and relevant CMS data security frameworks
• Own relationships with security auditors, compliance vendors, and healthcare IT governance bodies
• Monitor CMS policy updates and translate regulatory changes into actionable product and platform requirements

Cross-Functional Leadership

• Partner with product leadership to translate clinical and market requirements into technical specifications
• Collaborate with Sales and Customer Success to support hospital system procurement processes, IT security reviews, and go-live implementations

Qualifications

Required

• 10\+ years of progressive technology leadership experience, with at least 3–5 years as a VP of Engineering, CTO, or equivalent executive role
• Deep expertise in healthcare IT, specifically EHR integration, HL7 FHIR standards, and health data interoperability
• Proven track record of building and shipping SaaS products sold into hospital systems or large health systems
• Hands-on experience navigating HIPAA compliance, SOC 2 certifications, and healthcare data security frameworks
• Familiarity with CMS value-based care programs (e.g., MSSP ACO, MIPS/MACRA, hospital readmissions programs, quality payment programs)
• Strong executive presence with the ability to engage hospital CIOs, IT directors, and clinical leadership
• Supporting sales and strategy planning and execution
• Experience building engineering teams from early stage, including hiring, mentoring, and culture-setting

Preferred

• Direct experience with Epic or Cerner integration at scale (App Orchard, SMART on FHIR apps, certified integrations)
• Background in patient engagement, care management, or population health technology
• Experience working closely with CMS-regulated product categories (quality reporting, VBC performance measurement)
• Prior startup experience, ideally at a company that scaled through Series A/B within health tech

What We Offer

• Competitive salary and benefits package
• Hybrid work environment with flexibility (remote \+ on-site in the San Francisco Bay Area)
• Opportunity to shape scalable solutions that improve patient care and financial performance
• A mission-driven, collaborative team focused on real-world impact

We are an equal opportunity employer committed to building a diverse and inclusive team.