Executive Assistant (Job ID: MEGDEE1EAR)

Insideoutva; South Africa; Remote; ZAR 372,000 - 465,000; Full time

Job summary

Insideoutva is seeking an Executive Assistant to be the right hand to our Founder & CEO. This remote role focuses on high-trust, precise calendar management, inbox handling, travel logistics, and day-to-day operations.

Ideal candidates have excellent English, impeccable organizational skills, and a disciplined approach to security and AI-assisted workflows, with experience supporting senior leaders in a fast-moving remote setting.

Qualifications

• 3-5+ years as Executive/Personal Assistant supporting senior leaders in a remote setting.
• Exceptional spoken and written English.
• Uncompromising security discipline for accounts, 2FA, credentials, and access boundaries.
• Systems thinking and AI fluency to streamline workflows with human oversight.
• Experience using cloud tools and productivity suites (e.g., Google Workspace, Slack, Ramp).

Responsibilities

• Executive & Personal Administrative Ownership: manage calendar, inbox, travel, and internal workflows.
• Time & Priority Management: protect focus blocks, avoid double-bookings, prepare pre-meeting materials.
• Asynchronous Execution & SOP Management: refine and maintain documentation and SOPs.
• Inbox & Voice Alignment: draft emails and communications matching CEO tone.
• Security & System Maintenance: manage passwords, 2FA tokens, and permissions.
• AI-Assisted Problem Solving & QA: use AI thoughtfully with strict human oversight.
• Proactive Daily Reporting: provide daily asynchronous updates with priority statuses and blockers.
• Special Projects & Operational Support: support HR/finance/partners and prepare briefs.

Skills

Executive Assistant experience

English fluency

Security discipline

Systems thinking

AI fluency

Cloud tools proficiency

Tools

Google Workspace

Slack

Ramp

Job description

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

Are you an exceptionally precise, highly organized professional ready to act as a force multiplier for a high-velocity Founder & CEO? We are looking for a high-trust Executive Assistant to support a dynamic e-commerce brand specializing in functional medical accessories!

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: MEGDEE1EAR
• 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 on 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.

The ideal candidate possesses impeccable organizational skills, outstanding written and spoken English, disciplined technical judgment, and a proactive systems-thinking mindset—utilizing modern AI tools thoughtfully as an analytical partner to deliver complete, QA-checked solutions rather than bringing unsolved problems or unfiltered noise.

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: Drive transparent, daily asynchronous updates (via daily logging platforms like Cadence) outlining priority statuses, completed deliverables, and active blockers.
• Special Projects & Operational Support: Execute cross-functional administrative projects, interface with HR/finance/external partners, and prepare structured summaries, briefs, and action lists to speed up executive decision-making.

Qualifications & Skills

• 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, as well as capturing nuanced formal/informal writing styles.
• 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 to verify accuracy and context.
• High Systems & Cloud Fluency: Comfort operating across cloud software, Google Workspace (Gmail, Docs, Sheets, Calendar, Meet), Slack, and financial/operations hubs (e.g., Ramp).
• Receptive to Feedback & Fast Adaptation: Ability to process constructive feedback cleanly without defensiveness, adjusting execution style immediately to prevent recurring errors.

Non-Negotiables

• Zero-Tolerance for Security Errors: Absolute rigor when managing credentials, 2FA tokens, and access settings. Careless credential handling or missed security steps are immediate dealbreakers.
• Receptive to Feedback (No Defensiveness): Ability to accept direct feedback, acknowledge adjustments swiftly, and implement corrections without prolonged back-and-forth debates or excuses.
• Phone & Verbal Willingness: Complete comfort jumping on phone calls whenever digital options are unavailable (e.g., booking appointments, vendor coordination, or administrative follow-ups).
• Independent "Brain On" Judgment: High critical thinking skills. Uses AI as an efficiency tool rather than a replacement for logical reasoning, double-checking all automated outputs before escalation.
• Asynchronous-First & Documentation Mindset: Comfort operating in a documentation-first workflow, prioritizing written updates and clear progress tracking over unnecessary real-time meetings.
• Absolute Integrity & Confidentiality: Total discretion when handling sensitive inboxes, personal schedules, financial items, and business reputation.

Tech Stack

• Communication & Collaboration: Google Workspace (Gmail, Docs, Sheets, Calendar), Google Meet, Slack
• Finance & Operations: Ramp
• AI & Automation Tools: Claude, ChatGPT, specialized productivity AI software
• Daily Cadence & Progress: Operational logging and asynchronous status-tracking tools