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

Hunt St · Philippines · $2k – $2k · posted today ago

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About this role

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.