Head of AI Operating System

Raintree Systems

Head of AI Operating System at Raintree driving internal AI strategy and agentic workflows. Partnering with CEOs and ELT to ensure measurable business impact through AI initiatives.

Posted 6/5/2026full-timeRemote • 🇺🇸 United StatesLead💰 $220,000 - $250,000 per yearWebsite

Tech Stack

Tools & technologies

Open Source

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

AI strategyROI analysisagentic workflowsfrontier modelsMCP (Model Context Protocol)integration with LLM systemssemantic layersdata plumbingAI securityrisk management

Soft Skills

cross-functional alignmentleadershipcommunicationstrategic thinkingproblem-solvingcollaborationinfluence without authorityoperational excellenceanalytical skillsbusiness acumen