Remote Executive Assistant to CEO – AI-Savvy & Security-Focused

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

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.