Remote AI-Savvy Executive Assistant to Executives

Inside Out Hiring; United States; Remote; USD 20,000 - 24,000; Full time

Job summary

Inside Out Hiring is seeking an experienced Executive Assistant to partner with the ownership team across three assisted living facilities. You will manage inbox, calendar, coordinate with vendors, draft policies, and build dashboards tracking licensing and renewals.

You will apply AI tools to automate recurring tasks, develop playbooks, and support personal scheduling and travel for the owners. Strong English and US Central hours are required; remote work allowed.

Qualifications

• Career-level executive assistant experience supporting senior leaders, not entry-level VA work.
• Ability to exercise independent judgment and critical thinking.
• Fluency with AI tools such as ChatGPT and Claude, with dashboards/automations/SOPs experience.
• Availability to work US Central business hours regardless of home location.

Responsibilities

• Manage Inbox & Calendar for owners across multiple facilities.
• Coordinate vendor communications and scheduling for three facilities.
• Draft, format and maintain policies, SOPs, and operating playbooks.

Skills

Executive support

Independent judgment

AI tools proficiency

US Central hours

Tools

ChatGPT

Claude

Dashboard tools

Automation tools

Job description

Inside Out Hiring is seeking an experienced Executive Assistant to partner with the ownership team across three assisted living facilities. You will manage inbox, calendar, coordinate with vendors, draft policies, and build dashboards tracking licensing and renewals.

You will apply AI tools to automate recurring tasks, develop playbooks, and support personal scheduling and travel for the owners. Strong English and US Central hours are required; remote work allowed.