Chief of Staff, Strategic Operations & AI Workflows

About the role

Chief of Staff, Strategic Operations & AI Workflows

If you’re a healthcare-savvy operator who wants direct CEO leverage, company-wide scope, and a real mandate to turn strategy into AI-native operating systems, this is a high-impact seat. You’ll work side-by-side with the CEO of a fast-growing, VC-backed healthcare organization focused on last-mile delivery for value-based care—translating priorities, stakeholder friction, and ambiguous business problems into clear plans, practical workflows, and scalable execution.

The Opportunity

This is a strategy, operations, and AI workflow transformation role for someone who thinks like a product manager and operates like a builder. You’ll work across executives and functional leaders to understand what is slowing the business down, gather input from stakeholders, define requirements, prototype better ways of working, and drive adoption through iteration.

You will be close to company-wide decisions, leadership operating cadence, and cross-functional execution. The environment is fast-moving, high-ownership, and still being built—ideal for someone who has thrived in a scaling startup or growth-stage company where processes, systems, and roles were evolving quickly.

What You Will Own

CEO Leverage & Operating Cadence

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

Cross-Functional Strategy & Execution

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

AI-Native Workflow Transformation

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

What Makes You a Strong Fit

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

Compensation, Benefits & Work Model

Base salary: $170,000–$210,000

Bonus and equity

Health, dental, and vision insurance

401(k)

PTO

Remote role

Why This Role Matters

Your work will directly improve company velocity. You’ll help leaders focus on the right priorities, turn unclear problems into practical systems, and make business functions more efficient through better workflows, sharper operating cadence, and AI-native execution.

This is a strong fit if you like pace, ownership, and proximity to decision-making. You see problems, gather the right input, build a better way forward, and follow through until the business is operating better than it was before.

Apply now and get a response within 24 hours.