Head of AI Operating System

Job not on LinkedIn

🔥 12 hours ago

🇺🇸 United States – Remote

💵 $220k - $250k / year

⏰ Full Time

🔴 Lead

🤖 Artificial Intelligence

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Raintree Systems

WebsiteLinkedInAll Job Openings

201 - 500 employees

As the leading EMR for therapy and rehab, our all-in-one solution includes automated patient engagement, powerful revenue cycle management and billing in addition to flexible business intelligence. Schedule a free discovery call today! -> https://www.raintreeinc.com/schedule-a-demo

📋 Description

• Partner with the CEO and ELT to define Raintree's internal AI strategy and operating priorities; defend the roadmap with rigorous ROI analysis • Build and chair an executive AI council that sets policy, approves investments, and unblocks cross-functional work • Run the AI champions network — a working group of departmental representatives — as the operating engine of the program • Brief the board on AI program health, financial impact, and forward investment plan on a quarterly cadence • Navigate cross-functional alignment without direct authority • Architect and ship agentic workflows on frontier models (Claude, GPT, Gemini, leading open source) that automate or substantially augment real work across the business • Build the semantic and data layer that is the foundation of the entire program • Build MCP-based integrations into Salesforce, Slack, Gong, our ticketing systems, our finance and close tooling • Establish the evaluation, observability, and red-team practices that keep agents performant and safe in production • Build Raintree's AI governance framework • Track, validate, and report ROI

🎯 Requirements

• Top-tier academic background — leading university and quantitative discipline (Computer Science, Engineering, Mathematics, Physics, Economics, or similar) • Roughly 6–10 years of progressive experience, ideally a combination of: technical AI/ML work, top-tier strategy consulting (MBB) or operating role at a high-performance SaaS company, and at least one role where you built something from zero • Currently in a senior IC or director-track role at a strong company • Business mind first, AI specialist second • Real, recent, hands-on expertise applying frontier models (Claude, GPT, Gemini, leading open source) in production • Deep fluency with agentic workflows: planner-executor patterns, tool use, evaluation harnesses, observability, guardrails, human-in-the-loop design • Working knowledge of MCP (Model Context Protocol) and a track record integrating LLM systems with Salesforce, ticketing, Slack, Gong, finance and close tooling, and similar SaaS surfaces • Comfort designing and building semantic layers, retrieval architectures, and the data plumbing that makes agents reliable • Practical understanding of AI security, privacy, and risk: prompt injection, data exfiltration, audit logging, red-teaming, and HIPAA/PHI handling

🏖️ Benefits

• Comprehensive medical, dental, vision • 401(k) • Fully remote-first culture