Executive Assistant (Job ID: MEGDEE1EA)

Insideoutva; Northern (KY); Hybrid; USD 22,000 - 28,000; Full time

Job summary

Insideoutva is seeking an Executive Assistant to be the right hand to the Founder & CEO in a remote-first medical accessories e-commerce brand. You will offload administrative execution and daily operations to enable strategic growth, including calendar management, travel, email, and vendor coordination.

You will work with SOPs, access matrices, and voice/writing repositories, draft external communications in the CEO’s tone, maintain security protocols, and provide daily asynchronous updates.

Qualifications

• 3–5+ years of EA/PA experience supporting senior leaders in remote settings.
• Excellent spoken and written English communication.
• Strict discipline on security, credentials and access boundaries.
• Hands-on with AI integrations to streamline workflows while judging outputs.
• Fluency across cloud software including Google Workspace and Ramp.

Responsibilities

• Manage CEO calendar, inboxes, travel and internal workflows.
• Coordinate personal logistics and vendor arrangements.
• Own end-to-end calendar, protect focus blocks and prep materials.
• Draft emails and communications matching CEO tone and style.
• Maintain SOPs, access matrices and institutional knowledge.
• Produce daily asynchronous updates and support cross-functional projects.

Skills

EA/PA experience

English proficiency

Security awareness

AI fluency

Cloud tools

Tools

Google Workspace

Ramp

Slack

Job description

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

Are you a highly precise, proactive, and tech-savvy professional looking to become the ultimate right-hand to a visionary Founder & CEO? We are seeking an exceptional Executive Assistant to bring structure, security, and seamless execution to a fast-growing medical accessories e-commerce brand!

Job Details at a Glance

• Job Title: Executive Assistant

• Job ID: MEGDEE1EA

• Industry: Medical Devices / Healthcare Accessories & Supplies

• Location: LATAM / South Africa

• Job Status: Full Time

• Work Schedule: Monday to Friday, 8:00 AM to 5:00 PM / 7:00 AM to 4:00 PM PST

• Salary: $2000 to $2500 per month

• Target Start Date: ASAP

About the Client

Our client is a fast-growing, dynamic e-commerce brand specializing in functional and stylish medical accessories—including decorative adhesive tapes, overpatches, underpatches, and device stickers for continuous glucose monitors (CGMs) and insulin pumps. Led by a high-velocity Founder and CEO, operations run on robust documentation, clear processes, and a remote-first culture built around asynchronous productivity. We value high operational efficiency, proactive ownership, uncompromising security, and total integrity in every role.

About the Role

We are seeking a high-trust, exceptionally precise Executive Assistant to act as a force multiplier and right hand to our Founder & CEO.

In this role, your core mission is to offload administrative execution and daily operational friction from the CEO—spanning both business operations and personal life support (e.g., coordinating household vendors, appointment booking, and meal tracking during crunch periods)—enabling her to focus on strategic growth. Rather than relying on constant real-time meetings or micromanagement, you will step directly into a mature, well-documented environment featuring established Standard Operating Procedures (SOPs), detailed access matrices, and voice/writing repositories.

Key Responsibilities

Executive & Personal Administrative Ownership

• Manage high-level calendar scheduling, administrative inboxes, travel logistics, and internal team operational workflows.

• Support personal logistics (coordinating household services/vendors, meal tracking during intense periods, personal travel, and local bookings via digital tools or direct phone calls).

Time & Priority Management

• Own the CEO’s calendar end-to-end. Protect focus blocks, eliminate double-bookings, negotiate scheduling, and prepare comprehensive pre-meeting contexts, goals, and background materials independently.

Asynchronous Execution & SOP Management

• Work seamlessly from existing SOPs and permissions matrices, while continuously refining, creating, and maintaining documentation to preserve institutional memory.

Inbox & Voice Alignment

• Draft emails, messages, and external communications matching the CEO’s tone, nuance, and style guidelines across varied contexts.

• Filter communications intelligently—ensuring critical opportunities are highlighted without overwhelming the CEO with daily micro-decisions.

Security & System Maintenance

• Rigorously adhere to system administration protocols, managing passwords, 2FA tokens, and user permissions across digital platforms with high precision and zero security compromises.

AI-Assisted Problem Solving & Quality Assurance

• Utilize AI tools (e.g., Claude, ChatGPT) thoughtfully as an analytical thinking partner for research, drafting, and troubleshooting.

• Conduct strict human oversight and quality assurance (QA) on all AI outputs to ensure they reduce cognitive load rather than creating operational friction.

Proactive Daily Reporting & Special Projects

• Drive transparent, daily asynchronous updates outlining priority statuses, completed deliverables, and active blockers.

• Execute cross-functional administrative projects, interface with HR/finance/external partners, and prepare structured summaries to speed up executive decision-making.

Qualifications & Skills

Core Requirements:

• Proven EA/PA Experience: 3–5+ years of experience operating as an Executive Assistant and/or Personal Assistant supporting senior leaders, founders, or entrepreneurs in a remote setting.

• Exemplary Spoken & Written English: Superior written and verbal communication skills. Comfortable jumping on phone calls to book services or resolve operational inquiries.

• Flawless Technical & Access Security: Uncompromising discipline regarding account security, 2FA settings, credential safety, and strict permission boundaries.

• Systems Thinking & AI Fluency: Hands-on experience using AI integrations and productivity tools to streamline workflows while exercising human judgment.

• High Systems & Cloud Fluency: Comfort operating across cloud software, Google Workspace (Gmail, Docs, Sheets, Calendar, Meet), Slack, and financial/operations hubs (e.g., Ramp).

Non-Negotiables:

• Zero-Tolerance for Security Errors: Absolute rigor when managing credentials, 2FA tokens, and access settings. Careless credential handling is an immediate dealbreaker.

• Receptive to Feedback: Ability to accept direct feedback, acknowledge adjustments swiftly, and implement corrections without defensiveness or excuses.

• Phone & Verbal Willingness: Complete comfort jumping on phone calls whenever digital options are unavailable.

• Independent "Brain On" Judgment: High critical thinking skills. Uses AI as an efficiency tool, double-checking all automated outputs before escalation.

• Asynchronous-First Mindset: Comfort operating in a documentation-first workflow, prioritizing written updates over unnecessary real-time meetings.

• Absolute Integrity & Confidentiality: Total discretion when handling sensitive inboxes, personal schedules, and business reputation.

Tech Stack

• Communication & Collaboration: Google Workspace, Google Meet, Slack

• Finance & Operations: Ramp

• AI & Automation Tools: Claude, ChatGPT, specialized productivity AI software

• Daily Cadence: Operational logging and asynchronous status-tracking tools