Executive Assistant / Chief of Staff (AI-Driven, Operations & Life Management)

We are looking for someone who can think like an operator, not just take instructions
Executive Assistant / Chief of Staff (AI-Driven, Operations & Life Management)


Overview

We are looking for a high-performance Executive Assistant / Chief of Staff to support a fast-growing healthcare acquisition company and its CEO.

This is not a typical VA role.

You will act as a right-hand operator, helping manage business operations, communications, systems, and personal logistics. The ideal candidate is highly organized, tech-savvy, and capable of implementing AI tools to increase efficiency across the company.

You should be comfortable handling everything from email management and project coordination to travel planning and process automation.

This role is for someone who thrives in a fast-paced, entrepreneurial environment and wants to take ownership.


What You’ll Be Responsible For

???? Executive Support
• Manage and prioritize inbox (flag, draft, respond)
• Calendar management and scheduling
• Act as gatekeeper and organizer of priorities
• Draft clear, professional communications


?? Operations & Project Management
• Track key projects and ensure execution
• Build and maintain systems (Notion, Google Drive, etc.)
• Coordinate with team members and vendors
• Follow up relentlessly to keep things moving


???? AI & Automation
• Implement AI tools to improve workflows
• Set up automations (email sorting, task tracking, etc.)
• Help build internal dashboards and systems
• Continuously suggest efficiency improvements


?? Travel & Personal Management
• Book flights, hotels, and itineraries
• Optimize travel for time, comfort, and cost
• Handle personal admin tasks when needed
• Manage scheduling across multiple time zones


Ideal Candidate

You are:
• Extremely organized and detail-oriented
• Proactive — you solve problems before they arise
• Tech-savvy and comfortable with AI tools
• Clear and professional communicator
• Able to handle both business and personal responsibilities
• Calm under pressure and highly reliable


Preferred Experience
• Executive Assistant or Chief of Staff experience
• Experience supporting founders or entrepreneurs
• Strong with tools like:
• Google Workspace
• Notion / Asana / ClickUp
• ChatGPT / AI tools
• Experience managing email at scale
• Travel coordination experience

Compensation & Structure
• Full-time or part-time (flexible based on candidate)
• Remote
• Long-term role with growth potential

To Apply

Please include:
1. A 60 Second Video on why you an ideal fit for this role
2. Examples of systems or workflows you’ve built
3. Experience using AI tools in your work
4. Any experience supporting a founder or executive

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We are looking for someone who can think like an operator, not just take instructions

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