Executive Assistant (AI-capable)

The right candidate will be proactive, highly organized, and skilled in AI and technology to support the leadership team of a growing US-based non-emergency medical transportation business.

This role goes beyond traditional executive assistant duties. The ideal person will learn how the business operates, identify bottlenecks, use AI and automation to improve processes, and proactively take tasks off the founder’s plate.

The role will primarily focus on executive and administrative support, with some dispatch and booking backup during busy periods. Most booking activity is handled through an AI-powered system, with the candidate stepping in when human support is required.

Key Responsibilities:

Executive & Administrative Support

• Manage and triage the founder’s inbox, including HR-related and general inbound emails
• Organize, prioritize, and file emails and information appropriately
• Follow up on outstanding tasks, requests, and issues to keep things moving
• Take ownership of day-to-day administrative items and proactively identify things that need attention
• Support the GM and Director of Operations with administrative tasks as required
• Help reduce bottlenecks by taking ownership of tasks that would otherwise remain on the leadership team’s plate

Insurance & Claims Follow-Up

• Follow up on outstanding insurance claims and related enquiries
• Track claim progress and maintain clear records
• Communicate with relevant parties to obtain updates and resolve outstanding items
• Escalate issues when required and ensure follow-ups don’t fall through the cracks

AI, Automation & Technology

• Use AI tools such as Claude, ChatGPT, and other automation platforms to improve day-to-day workflows
• Help identify opportunities to automate repetitive administrative processes
• Assist with the adoption of AI tools across the business
• Help build a culture of using technology and automation to work more efficiently
• Learn and work within the company’s EOS (Entrepreneurial Operating System) processes and dashboards
• Help monitor KPI dashboards and flag anything that requires attention
• Support the implementation and rollout of Salesforce CRM
• Help organize and improve digital systems and workflows as the business grows

File & Systems Organization

• Reorganize and maintain the company’s SharePoint drive and folder structure
• Improve how documents and information are stored and accessed
• Help establish practical systems for keeping information organized

Dispatch & Booking Backup

• Provide backup support for dispatch and booking during peak periods
• Monitor incoming booking or dispatch requests and assist when human intervention is required
• Support the existing AI-powered booking process and step in when issues need to be resolved manually
• Assist with dispatch-related administration and communication as needed
• Provide additional support during busy periods, staff shortages, or other operational bottlenecks

Requirements

Required Skills and Qualifications:

The ideal candidate will:

• Have previous experience as an Executive Assistant, Virtual Assistant, Operations Assistant, Administrative Assistant, or similar
• Have experience supporting a founder, executive, or senior leadership team
• Be highly organized and comfortable managing multiple priorities
• Have excellent written and verbal English
• Be confident using AI tools such as Claude and ChatGPT
• Understand how AI and automation can be used to improve business processes
• Be comfortable learning new software and systems quickly
• Have strong attention to detail and follow-through
• Be comfortable working independently without needing constant direction
• Be confident following up with people and keeping tasks moving
• Have a practical, problem-solving mindset
• Be willing to learn how the business operates and proactively identify ways to help

Dispatch / Operations Experience

Experience in any of the following would be highly regarded:

• Dispatch or transportation coordination
• Booking or scheduling
• Logistics or fleet coordination
• Customer service in a transport or healthcare environment
• Non-emergency medical transportation (NEMT)
• Working with dispatch, scheduling, or booking software
• Supporting an operations team in a fast-paced environment

You don’t need to have experience in every area. We’re particularly interested in someone who can combine strong administrative skills with initiative, technology skills, and a willingness to learn.

The Right Mindset

This role is intentionally not a tightly defined checklist of tasks. We’re looking for someone who can come in, learn how the business works, understand where the pressure points are, and start taking ownership.

For example, rather than waiting to be told that a KPI needs attention, the right person might notice something has changed, investigate it, and flag it to the appropriate person.

Likewise, if a repetitive administrative process can be improved with AI or automation, we’d want this person to identify the opportunity and help implement a better way of doing it.

Initiative, ownership, and curiosity will be just as important as previous job titles.