Executive Assistant (Job ID: ETTREG1EA)

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

Exciting Remote Opportunity! We're Hiring an Executive Assistant!

Are you a career-level administrative professional ready to be a proactive partner to an ownership team? We are looking for an AI-fluent Executive Assistant to support the leaders of a growing group of assisted living facilities!

IMPORTANT - Watch this quick Loom video on how to get hired:

https://www.loom.com/share/345f776084e642ba99c24aabe40a67a0

C1 ENGLISH LEVEL IS REQUIRED. The selected candidate will be speaking strictly in English during their whole shift.

Job Details at a Glance

• Job Title: Executive Assistant

• Job ID: ETTREG1EA

• Industry: Assisted Living Facilities

• Location: LATAM preferred or South Africa

• Job Status: Full Time

• Work Schedule: Monday to Friday, 8:00am to 5:00pm Central Time

• Salary: $2000 per month

About the Client

The company operates a group of three assisted living facilities in North Branch, Minnesota, providing residential and clinical care to residents while managing the administrative, vendor, and regulatory functions that support each property. Ownership is split between administrative and operational oversight on one side and clinical leadership on the other, with on-site front desk and HR staff supporting day-to-day facility operations.

This role exists because the owners currently absorb a high volume of administrative work themselves, including correspondence, scheduling, vendor follow-up, and policy and procedure documentation, which limits the time available for higher-level planning and growth of the business. Existing on-site staff are focused on resident and vendor-facing work or HR and benefits administration, leaving no dedicated support for the owners at the executive level.

About the Role

You will serve as a direct, proactive partner to the ownership team, managing inbox and calendar activity, coordinating with vendors, and handling scheduling across multiple facilities. You will draft, format, and organize policies, procedures, and standard operating documents, and build trackers and dashboards that bring visibility to recurring obligations such as licensing and renewals.

You will apply AI tools to streamline recurring work, build automations, and develop playbooks that reduce reliance on verbal instruction over time. Beyond core administrative tasks, you will take on personal scheduling and travel coordination support, and you will be expected to exercise independent judgment, flag issues proactively, and bring forward solutions rather than waiting for direction.

Key Responsibilities

• Inbox & Calendar Management: Own day-to-day email triage, scheduling, and calendar coordination for both owners across a demanding, service-based operation.

• Vendor Communications: Manage correspondence, follow-ups, and scheduling with vendors supporting three assisted living facilities.

• Policy & SOP Development: Draft, format, and maintain policies, procedures, and standard operating playbooks for ownership and other staff.

• Dashboards & Tracking: Build and maintain trackers and dashboards covering licensing, renewals, and other recurring operational obligations.

• AI-Driven Workflow Automation: Use ChatGPT, Claude, and related tools to automate recurring tasks and improve process efficiency.

• Personal Administrative Support: Coordinate travel arrangements and personal scheduling on behalf of the owners.

• Proactive Right-Hand Support: Anticipate needs, exercise independent judgment on routine matters, and elevate only decisions that require owner input.

• HR Assistance: Handling admin, recruitment process, and payroll.

Qualifications & Skills

Core Requirements (Non-Negotiable):

• Career-level executive assistant experience supporting senior leaders or executives, not entry-level virtual assistant experience.

• Demonstrated ability to exercise independent judgment and critical thinking rather than relying solely on step-by-step instructions.

• Fluency with AI tools such as ChatGPT and Claude, with demonstrated ability to build dashboards, trackers, automations, and SOPs.

• Availability to work US Central business hours regardless of home location.

Additional Requirements:

• Strong written and verbal English communication skills suitable for direct, daily interaction with senior leadership and external vendors.

• Comfort handling sensitive administrative and financial coordination tasks within defined access limits and approval processes.

• Preference for full-time engagement, reflecting the scope and continuity required by the role.

Tech Stack:

• ChatGPT and Claude

• Calendar software and Email platform

• Dashboard/tracker tools

• Workflow automation tools

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