Executive Virtual Assistant – Email & Calendar Management (Full-Time)

About the role
We're a small, fast-moving team looking for a sharp, proactive Executive VA to completely own our inboxes and calendars. This is a full-time role requiring significant overlap with US Central time. You'll work inside our Microsoft 365 environment — including Outlook and our trained Microsoft Copilot agent — to keep two executives organized, responsive, and focused. If you thrive on structure, hate letting things slip, and are excited to work alongside AI tools rather than around them, this role is for you.

Core responsibilities

Email management
Triage inboxes for two tea ---------- mbers daily — categorize, organize, and prioritize incoming email
Use our Copilot AI agent to generate draft responses, then review each draft for accuracy and tone before surfacing for approval
Flag high-priority emails that require personal attention, with a brief note explaining why
Build and maintain a clean folder, label, and rules structure in Outlook
Ensure no email goes unresponded beyond 24 hours — escalate anything at risk of slipping
Calendar & scheduling
Own scheduling for two people — book, confirm, and reschedule meetings in Outlook Calendar
Proactively flag and resolve calendar conflicts before they become problems
Send timely reminders and prep notes ahead of important meetings
Coordinate across time zones with external contacts as needed
You're a great fit if you:
Have 2+ years supporting executives with email and calendar management
Are comfortable working inside Microsoft 365 — Outlook, Outlook Calendar, and ideally Copilot or similar AI tools
Exercise strong judgment — you know the difference between what needs a human decision and what can be handled
Write clear, professional English and can spot when an AI-generated draft needs refinement
Are available during US Central business hours (8am–5pm CST)
Communicate proactively — you flag issues before we notice them

To apply, please include:
A summary of your email and calendar management experience
Any AI or automation tools you've used in an admin context (Copilot, ChatGPT, Zapier, etc.)
A brief example of how you'd handle this scenario: You receive 47 emails overnight. Walk us through how you'd triage them and what you'd surface first.