AI Automation Lead | Associate Chief of Staff & Executive Assistant to CEO

About the Opportunity Atlas Medical Data Group (AMDG) is a healthcare data and technology company. We work with healthcare providers to improve how they operate - better rates, better technology, better infrastructure - using data and AI as the foundation. AI isn’t a feature for us; it’s built into how we work. We’re hiring an AI Automation Lead to serve as Associate Chief of Staff and Executive Assistant to the CEO. The job is to make sure all executive support and operations are managed efficiently and effectively and to automate as much of it as possible. As the person in this role automates more of the executive assistant responsibilities, they'll create the bandwidth for themselves to take on other strategic responsibilities. This is a remote-first position, but we would prefer candidates in the Kansas City area where the founder/CEO is based. Role Overview This role is essentially a technical associate Chief of Staff position, with executive assistance as the first and most immediate responsibility. The initial mandate is to make sure the executive support function runs effectively (calendar management, inbox oversight, scheduling, travel, meeting prep, action-item tracking) and to automate as much of that as possible, as quickly as possible. Whatever isn't automated at any given point still needs to get done, and this person owns that. The automation work is central to the role. We want this person actively building AI agents, workflows, and systems that reduce the manual effort required to keep the CEO organized and operating effectively. The faster that happens, the more capacity opens up for broader strategic and operational work. As that capacity is created, the scope of the role expands. Who We’re Looking For We're looking for someone who is already building with AI, exceptionally organized, and ready to take on real operational responsibility. Prior executive assistant experience isn't required - what matters is a builder's orientation, organization, and attention to detail. Strong candidates come from a range of backgrounds, but they all share one thing: they are already building with AI. The bar here isn't using AI for productivity (drafting emails, summarizing documents, etc). It's using AI as a development tool to write and ship code and build real automation. That means working in coding environments like Cursor, Claude Code, or Codex. Having some foundation in a language like Python or JavaScript is ideal but not required. They should be able to speak to what they've built clearly and specifically - what it does, how they built it, what problems it solves. Beyond that, we’re looking for someone with a track record of high performance and a habit of teaching themselves things independently. A business or finance background combined with genuine AI development ability is just as strong a profile as a technical one. This role needs both the business and technical dimensions, and someone who only wants one won’t be a fit. Key Responsibilities Manage the CEO’s inbox, calendar, scheduling, and daily logistics Automate executive calendar management, scheduling, and administrative logistics using AI tooling and workflow automation platforms Build AI-driven systems for inbox curation, triage, prioritization, and response drafting Automate travel booking, itinerary creation, and trip planning workflows Coordinate meeting preparation, action-item tracking, and cross-team project planning Elicit and document CEO preferences to build customized AI agent behavior and repeatable systems Test and evaluate emerging AI tools; integrate successful solutions into daily workflows Scale successful automations across additional executives and eventually organization-wide Build custom solutions and automations using leading AI tools and capabilities Create and maintain AI skills, agent configurations, and preference profiles Document workflows and systems to enable consistent execution and scaling Take on broader strategic and operational responsibilities as automation frees up time to expand scope Required Qualifications Already building with AI - writing and shipping code using tools like Claude Code, Cursor, or Codex and/or working with agent frameworks and SDKs to build and deploy real automations and agentic workflows. Can speak to what they've built clearly and specifically. Exceptionally organized. The kind of person where it's obvious - in how they think, how they communicate, how they manage their time, and how they structure their work. Understanding of what executive support requires and authentic willingness to own that work A track record of high performance - whether through academic achievement, progression at high-caliber organizations, or demonstrated results in prior roles Self-directed learner who has taught themselves meaningful skills outside of any job requirement - a recurring pattern, not a one-time instance Comfortable in a fast-moving, ambiguous environment with a startup pace Strong written and verbal communicator who can represent the CEO externally with professionalism and clarity Preferred Qualifications Technical, STEM, or business degree or equivalent demonstrated background Experience building agentic workflows or multi-agent systems using frameworks like LangChain, LangGraph, CrewAI, AutoGen, or similar Prior exposure to executive support, project coordination, or operations in a fast-growth environment Experience with calendar-automation, email-automation, or meeting-intelligence tooling Familiarity with prompt engineering and the ability to design reliable, production-grade AI interactions