Executive Assistant (AI-capable) (024-1369)

Looking for Philippines-based candidates

Job Role: Executive Assistant (AI-capable)

Compensation range: $1,500 USD - $2,000 USD / Monthly

Engagement type: Independent Contractor Agreement

Work Schedule: This role is expected to align with the client’s US business hours (approx. 9 AM - 5 PM, Monday to Friday, client’s time zone) for collaboration, but as a contractor, you’ll have flexibility in how you manage your time.

Who We Are: At Hunt St, we help Australian and US companies hire top remote talent in the Philippines. For this role, you will be engaged directly by the client as an independent contractor. We are not an outsourcing agency. All of our roles are 100% remote so you'll be able to work from home.

Who The Client Is: Our client is a growing US-based non-emergency medical transportation provider, helping people with mobility needs get safely to medical appointments and essential destinations. The business is focused on reliable service and efficient operations, and is now looking to strengthen its systems, embrace AI, and support its growing team.

Role Overview: We’re looking for a proactive, highly organised Executive Assistant with strong AI and technology skills to support the leadership team of a growing US-based non-emergency medical transportation business.

This is more than a traditional EA role. The right person will be someone who can learn how the business operates, identify bottlenecks, use AI and automation to improve processes, and take things off the founder’s plate without always being asked.

The role will primarily focus on executive and administrative support, with some dispatch and booking backup during busy periods. Most booking activity is expected to be handled through an AI-powered system, with the successful 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
• Organise, prioritise 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 organise and improve digital systems and workflows as the business grows

File & Systems Organisation

• Reorganise 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 organised

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:

What We're Looking For

We're looking for someone who is proactive rather than purely task-driven.

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 organised 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.

Working Hours

• Full-time position
• Must be available to work US Central Time business hours
• Remote / work-from-home
  

Compensation

USD 1,500–2,000 per month, depending on experience and capabilities.

There may also be an opportunity for an additional performance-based incentive or bonus structure following an initial 30–60 day performance review. This would be tied to agreed goals and performance outcomes.

Engagement

• Independent Contractor Agreement (ICA)
• Long-term opportunity for the right person
• Direct engagement with the business
• Clear performance expectations and agreed contract terms

Why This Role Is Different

This is an opportunity for someone who wants to be more than an administrative pair of hands.

You'll have the opportunity to work closely with leadership, influence how technology and AI are used within the business, improve systems and processes, and take genuine ownership of areas that make a difference to the day-to-day operation.

Work Arrangement & Expectations:

This is a remote role that will be set up as an independent contractor engagement.

To ensure alignment and transparency, successful candidates will be expected to:

• Disclose any existing ongoing roles or client work
• Reflect this engagement on their LinkedIn profile (clearly marked as “Independent Contractor”)