Remote Executive Assistant to Founder & CEO

Inside Out Hiring; United States; Remote; USD 22,000 - 28,000; Full time

Job summary

Inside Out Hiring is seeking a highly organized Executive Assistant to support a fast-moving Founder & CEO in a fully remote role. The ideal candidate will handle calendar management, inbox duties, travel planning, and high-level administrative tasks with a focus on security, accuracy, and proactive problem-solving.

You will operate in a documented, asynchronous-first environment, using SOPs and voice/writing repositories, and leverage AI tools thoughtfully to deliver QA’d outputs while

Qualifications

• 3–5+ years of EA/PA experience supporting senior leaders remotely.
• Excellent spoken and written English.
• Flawless security discipline regarding access controls and credentials.
• Experience using AI tools to streamline workflows with human oversight.

Responsibilities

• Manage CEO calendar, email inbox, travel logistics, and internal workflows.
• Protect focus blocks, prevent double-bookings, and prepare pre-meeting context.
• Refine and maintain SOPs and documentation for institutional memory.
• Draft emails and messages matching CEO tone across contexts.
• Manage passwords, 2FA tokens, and permissions across platforms with high accuracy.
• Use AI thoughtfully as a partner for research, drafting, and QA of outputs.
• Provide daily asynchronous status updates with priority, blockers, and deliverables.
• Lead cross-functional administrative projects and liaise with HR/finance/external partners.

Skills

Executive EA experience

English proficiency

Security discipline

AI fluency

Systems thinking

Cloud literacy

Tools

Google Workspace

Slack

Ramp

AI tools

Job description

Inside Out Hiring is seeking a highly organized Executive Assistant to support a fast-moving Founder & CEO in a fully remote role. The ideal candidate will handle calendar management, inbox duties, travel planning, and high-level administrative tasks with a focus on security, accuracy, and proactive problem-solving.

You will operate in a documented, asynchronous-first environment, using SOPs and voice/writing repositories, and leverage AI tools thoughtfully to deliver QA’d outputs while