Chief of Staff, Strategic Operations & AI Workflows

Urrly•Austin, TX

11d•$170,000 - $210,000•Remote

About The Position

This is a high-impact seat for a healthcare-savvy operator who wants direct CEO leverage, company-wide scope, and a mandate to turn strategy into AI-native operating systems. The role involves working side-by-side with the CEO of a fast-growing, VC-backed healthcare organization focused on last-mile delivery for value-based care. The primary focus is translating priorities, stakeholder friction, and ambiguous business problems into clear plans, practical workflows, and scalable execution. This is a strategy, operations, and AI workflow transformation role for someone who thinks like a product manager and operates like a builder. The individual will collaborate across executives and functional leaders to identify business slowdowns, gather stakeholder input, define requirements, prototype improved ways of working, and drive adoption through iteration. The environment is fast-moving, high-ownership, and still being built, making it ideal for individuals who have thrived in scaling startups or growth-stage companies with evolving processes, systems, and roles.

Requirements

Healthcare exposure through an operating role, consulting, investing, banking, healthcare services, or a closely adjacent environment
Strategy experience from consulting, business operations, product operations, startup operations, or a formal strategy role
Experience in a fast-growing startup or scaling company where you operated in ambiguity, built processes, and wore multiple hats
Direct experience working with or reporting to a CEO, founder, executive, or senior operating leader
A product-oriented mindset: you can discover stakeholder needs, translate pain points into requirements, and improve solutions through iteration
Hands-on experience using AI-assisted development or workflow tools such as Claude Code, Codex, Cursor, or similar systems to solve real business problems
Proven ability to deliver complex, cross-functional projects with multiple stakeholders and competing priorities
Strong executive-level writing, communication, synthesis, and judgment
Advanced comfort with spreadsheets, dashboards, workflows, and modern operating tools

Nice To Haves

Experience in value-based care, Medicare, Medicaid, ACA, payer-facing healthcare, or broader healthcare services
Prior Chief of Staff, BizOps, strategy, product operations, startup operations, or CEO-adjacent experience
Background in a VC-backed or high-growth environment where teams, systems, and operating processes scaled quickly
Hands-on experience building lightweight internal tools, dashboards, prototypes, automations, or workflow improvements for business users

Responsibilities

Partner directly with the CEO on strategic priorities, executive agendas, prep, follow-ups, and decision memos
Help align leadership around OKRs, KPIs, operating rhythm, and the highest-priority company initiatives
Build and maintain practical dashboards, workflows, and materials that improve visibility and follow-through
Support board-adjacent and executive-level materials with crisp writing, clear analysis, and strong judgment
Drive initiatives that cut across finance, operations, product, people, and functional teams
Bring structure, urgency, and accountability to complex multi-stakeholder projects
Identify blockers, clarify owners, and help leaders move from ambiguous problems to concrete execution plans
Lead special projects that may include AI rollout, operating model design, new growth channels, integration work, or business process redesign
Re-architect functional workflows with executives and operating leaders using AI-native approaches
Interview stakeholders, identify pain points, and translate feedback into clear requirements
Use tools such as Claude Code, Codex, Cursor, or similar AI-assisted builders to prototype lightweight solutions, dashboards, workflows, or internal tools
Pressure-test solutions with stakeholders, gather feedback, improve the workflow, and drive practical adoption