Executive Operations Assistant to Healthcare CEO

General Must‑Have’s

• Must have worked directly for startup founders
• Currently employed and open to a new opportunity
• Has previously run QuickBooks Online
• Has previously run ADP
• Extremely reliable; uses virtual tracking for themselves and others so time and output are always visible
• Thrives in a fast‑paced environment and can create steadiness, process, and organization during chaos
• Open to a $60–70k base, with the understanding that bonus opportunities can bring total comp to where you need it

AI Skills

• Has built automations between software tools
• Uses automations to remove human labor, increase efficiency, and keep operations organized
• Knows how to create agentic workflows using OpenClaw, Perplexity, or Claude
• Regularly uses agentic tools and can share a Loom video demonstrating an automation and an agentic workflow they personally built
• Operates with the mindset: “If I do the same task more than twice, I automate it.”

Calendar Management

• Always knows what’s in the CEO’s calendar at least one week ahead
• Prepares concise notes and proposed agendas; references prior emails, last meeting details, and any relevant data
• Uses flawless language when rescheduling or communicating changes
• Follows up on all action steps after every meeting

Project & Task Management

• Extremely organized and meticulous
• Comfortable maintaining a very large, dynamic task list
• Uses a task manager with automation and reminders
• Never lets a task, email, or follow‑up fall through the cracks

Finance & Budgeting

• Fluent in the latest versions of QuickBooks and ADP, and willing to handle all tasks within those platforms
• Able to maintain a tight budget and proactively remove unnecessary expenses
• Familiar with tax strategy — enough to keep the company forward‑thinking and always prepared

HR & People Operations

• Very fluent in US employment law and able to handle write‑ups when needed
• Can update agreements, maintain HR documentation, and stay on top of all compliance elements
• Excellent at recruitment and hiring; comfortable with terminations when necessary

Healthcare Relevance

• Understands enough about insurance to occasionally call for credentialing applications
• Familiar with licensure requirements and able to keep everything organized and up to date
• Knows HIPAA and Medicare and ensures the team stays compliant

Autonomous Task Completion

• Does not need to ask for help 90% of the time — uses AI, help desks, YouTube tutorials, etc. to self‑solve
• Saves questions for 1:1s in an organized way, with relevant screenshares prepared
• Must be able to work independently and be fully trustworthy without CEO oversight

Work Style

• VERY organized, focused, and has an exceptional attention span
• Able to create calm, structure, and clarity in a high‑velocity environment

Personal Assistance to CEO

• Comfortable booking personal appointments (e.g., doctor’s appointments) during work hours — with a signed agreement
• Lives in Miami (or willing to relocate)
• Willing to help with occasional in‑person needs (e.g., weekday pickups/drop‑offs, errands)
• Supports travel planning and logistics

Pay: $55,000.00 - $65,000.00 per year

Work Location: Hybrid remote in Miami Beach, FL 33141