Executive Assistant (Job ID: JARDEE1EA)

Inside Out Hiring; United States; Remote; USD 27,552,000 - 38,573,000; Part time

Job summary

Inside Out Hiring is seeking a sharp, AI-fluent Executive Assistant to support a rapidly scaling executive team with logistics, office launches, and operations for a medical certification training network.

This remote, part-time role starts at 30 hours per week, with a path to full-time, and pays $12.50/hour (approximately $2,000/month at 160 hours). You will split time between the Founder/CEO and Site Setup Lead, with future expansion to an Operations Lead stream.

Qualifications

• 2+ years of experience as an executive assistant, virtual assistant, or operations support specialist.
• Hands-on experience using AI tools (ChatGPT, Claude, etc.) daily to speed up research, drafting, reporting and data tasks.
• Strong written and verbal English communication with reliable follow-through on multi-week tasks.

Responsibilities

• Coordinate executive travel, logistics, and calendars across time zones.
• Draft routine correspondence and track action items for executives.
• Leverage AI tools to build deliverables, research markets, and improve workflows; create SOPs and dashboards.
• Support office launches: vendor coordination, billing setups, landlord communications, and data maintenance.

Skills

AI proficiency

Executive support

English communication

Reliability

Tools

Google Sheets

Excel

Google Workspace

Dropbox

Job description

We're Hiring: Executive Assistant

Are you a sharp, AI-fluent professional looking to provide multi-functional support to a rapidly scaling executive team? We are looking for an Executive Assistant to manage logistics, office launches, and operational functions for an innovative medical certification training network!

Job Details at a Glance

• Job Title: Executive Assistant

• Job ID: JARDEE1EA

• Industry: Automated Medical Certification Training

• Location: Philippines / LATAM / South Africa

• Job Status: Part-Time (30 hrs/week to start), with a realistic path to Full-Time (~40 hrs/week)

• Work Schedule: Monday to Friday, within approximately 8:00 AM to 5:00 PM Pacific Time

• Salary: $12.50 per hour ($2000 for full time - 160 hours per month)

• Target Start Date: ASAP

About the Client

The company operates an automated medical certification training network built around unmanned, voice-enabled training stations that guide medical professionals through certification processes in partnership with a leading national medical association. The business currently operates dozens of locations nationwide and is scaling rapidly, with plans to more than triple its footprint over the next two years. Its model combines site selection technology, lease negotiation, and rapid deployment to bring new locations online within weeks of signing.

The role exists because the founder's time is increasingly consumed by administrative work that does not scale with the business: travel logistics, lease and contract coordination, insurance paperwork, file organization, and other recurring tasks. As the company accelerates its expansion pace, the founder requires dedicated support to protect time for high-value activities such as market expansion and partnership development.

About the Role

We are hiring a sharp, AI-fluent Virtual Assistant to provide multi-functional support across executive, office launch, and operational functions. You will initially split 25–30 hours/week between two primary executives: Jarrod (Founder & CEO) and Cristy (Site Setup Lead).

As our team expands, this role is structured to pick up a third workstream supporting our incoming Senior Operations Lead, transitioning the position to a full-time role (~40 hrs/week).

Key Responsibilities

Founder & CEO Support — Jarrod (~15 hrs/week)

• Executive & Personal Logistics: Coordinate business and personal travel (flights, hotels, itineraries). Manage household and family coordination tasks, appointments, and reservations.

• Execution & Correspondence: Track action items and meeting follow-ups to keep commitments on schedule. Draft routine correspondence on Jarrod's behalf (note: inbox/calendar are self-managed).

• AI & Reporting: Utilize AI tools (ChatGPT, Claude) daily to build deliverables, research markets/competitors, and optimize workflows. Draft SOPs, build recurring spreadsheets/dashboards, and flag automation opportunities.

• File Management: Maintain and clean up Google Drive and Dropbox folder structures, de‑duping and archiving files.

Site Setup Support — Cristy (~10–15 hrs/week)

• Office Launch Admin: Support administrative pipelines for new office launches, tracking checklist items, shipping management, vendor coordination, and market research.

• Billing & Landlord Setup: Coordinate initial billing setups for new locations (landlord portal creation, ACH/autopay enrollment, Ramp account setup). Directly contact landlords to resolve missing invoices, portal access, and payment confirmations.

• Data Maintenance: Maintain accurate records and status trackers across operating tools to ensure launches do not stall.

Operations Lead Support (Future Workstream — ~10 hrs/week)

• Documentation & Tracking: Maintain operations manuals and update SOPs as new processes are established. Track progress across automation and process‑improvement projects.

• Coordination: Manage handoffs, scheduling, and documentation between the Ops Lead, internal team, and external contractors.

Qualifications & Skills

Core Requirements:

• Experience: 2+ years of experience as an executive assistant, virtual assistant, or operations support specialist.

• AI Proficiency: Hands‑on experience using AI tools (ChatGPT, Claude, etc.) daily to speed up research, drafting, integrated reporting across multiple tools, and related data tasks.

• Technical Skills: Intermediate spreadsheet proficiency (Google Sheets/Excel formulas and data cleanup); experience with Google Workspace and Dropbox.

• Communication & Reliability: Clear, professional written and verbal English communication skills with strong follow‑through on multi‑week tasks with minimal oversight.

Preferred Qualifications:

• Prior experience supporting startup founders, small business owners, or multi-location/franchise operations.

• Familiarity with project trackers (Asana), spend management tools (Ramp), or accounting tools (QuickBooks).

• Basic AP‑adjacent experience (coordinating billing, vendor onboarding, or landlord logistics).