Executive Assistant to CEO — Remote-First, AI-Savvy Ops

Insideoutva; South Africa; On-site; ZAR 359,000 - 448,000; Full time

Job summary

Insideoutva seeks an Executive Assistant to be the Founder & CEO’s right hand in a remote-first, process-driven environment. The role focuses on offloading administrative execution, calendar management, travel logistics, and personal life support to enable strategic growth.

You will work with established SOPs, maintain security protocols, draft communications in the CEO’s tone, and QA AI outputs. A fast-growing e-commerce brand with async workflows awaits a proactive, meticulous organizer.

Qualifications

• 3–5+ years of experience as an Executive Assistant or Personal Assistant supporting senior leaders in a remote setting.
• Superior written and verbal English communication skills.
• Uncompromising discipline on account security, 2FA, and access boundaries.
• Hands-on experience with AI integrations to streamline workflows while using human judgment.
• Comfort operating across cloud software and collaboration tools.
• Ability to process feedback and adapt quickly without defensiveness.

Responsibilities

• Manage CEO calendar, inbox, travel logistics, and internal workflows.
• Coordinate personal logistics (household services, meals, bookings) during crunch periods.
• Prepare pre-meeting contexts, goals, and background materials independently.
• Draft emails and messages matching the CEO’s tone across contexts.
• Maintain SOPs, access matrices, and documentation for institutional memory.
• Ensure security protocols, passwords, 2FA, and permissions are rigorous.
• Apply AI tools thoughtfully as an analytical partner with QA on outputs.
• Provide daily asynchronous updates outlining priorities, deliverables, and blockers.
• Lead cross-functional administrative projects and brief/action lists for faster decisions.

Skills

EA/PA Experience

English Proficiency

Security & Access

Systems Thinking

AI Fluency

Cloud Proficiency

Independent Judgment

Tools

Google Workspace

Ramp

Claude

ChatGPT

Slack

Job description

Insideoutva seeks an Executive Assistant to be the Founder & CEO’s right hand in a remote-first, process-driven environment. The role focuses on offloading administrative execution, calendar management, travel logistics, and personal life support to enable strategic growth.

You will work with established SOPs, maintain security protocols, draft communications in the CEO’s tone, and QA AI outputs. A fast-growing e-commerce brand with async workflows awaits a proactive, meticulous organizer.