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AI Chief of Staff and Operations

HealthEx | Full-time | Bay-area

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About HealthEx

HealthEx is building the infrastructure layer for consumer-permissioned health data - think Plaid, but for health records. We connect individuals to their clinical data across TEFCA, FHIR, and QHIN networks, and power AI experiences at companies like Anthropic, Microsoft and Salesforce. We are looking for an AI Operations Lead / Chief of Staff to work directly with the CEO across three equal functions: building and deploying AI solutions internally, driving cross-functional strategic execution, and supporting product and commercial initiatives as we scale.

Role overview

Chief of staff/strategic execution & operations

Partner with the CEO on company priorities, strategic planning, and high-stakes decisions
Drive execution of cross-functional initiatives that don't have a clear home
Prepare board decks, investor updates, and internal strategy memos
Identify bottlenecks and implement scalable processes across the company
Define and track key operational and commercial metrics across the company
Act as a communication bridge across engineering, clinical, and business teams — translating requirements clearly and without losing fidelity
Coordinate and support CEO communications and external-facing materials

Build and deploy internal AI solutions

Identify, prioritize, design, and build AI-powered workflows for the activities above — using Claude, Claude Code, and agentic tooling
Write code when needed, and orchestrate AI agents when that's faster
Ensure AI solutions are deployed safely, effectively, and in compliance with HIPAA and applicable healthcare data regulations — with appropriate guardrails, evaluation frameworks, and monitoring in place

Product and growth support

Contribute ideas and insights to product strategy for new strategic efforts, drawing on your AI expertise
Help define go-to-market and pilot strategies with strategic healthcare partners
Contribute to hiring plans and organizational design as we scale

What you'll bring

Healthcare or health tech experience
Familiarity with FHIR, TEFCA, or health data interoperability
Experience in HIPAA-regulated or other regulated data environments
MCP or API integration experience
Prior startup or operator role

What we value most:

You do and build things. You don't just advise on them or wait for direction.
You learn domains quickly — clinical workflows, TEFCA nuance, enterprise sales motion - whatever the problem requires
You bring new thinking. We want someone earlier in their career who sees possibilities the rest of us might miss.
You communicate crisply across technical and non-technical audiences, in writing and in person
You're energized by a fast-moving environment with real stakes

This role is for doers and builders who can also zoom out. If your instinct when you see a manual process is to automate it, we want to talk to you.

Qualifications

4-8 years of experience in startups, product, operations, engineering, or similar roles
Code writing ability - you can build, not just direct
Fluency with Claude and LLMs, including agentic tooling (Claude Code, Cowork)
Proven ability to manage complex projects across multiple stakeholders
Strong cross-functional communication skills across technical and non-technical audiences
Structured thinking and comfort operating in ambiguity
Bay Area based