Virtual Assistant — Email, Admin & Personal Support

I’m a busy professional in Chicago with a full-time job and a growing side hustle. I’m hiring my first VA to help me reclaim my time so I can focus on what actually moves the needle.

This is a long-term role for someone who is proactive, detail-oriented, and communicates clearly. I’m not looking for someone to just follow a checklist — I want someone who thinks ahead, flags problems before they become issues, and takes real ownership of their tasks.

We’ll start with a paid trial task, and if it’s a great fit, this grows into an ongoing role with more responsibility over time.

WHAT YOU’LL BE DOING

Email & Calendar
• Daily inbox triage — flag what needs me, archive the rest
• Unsubscribe from junk and keep my inbox clean
• Schedule meetings and personal appointments
• Send me a brief weekly summary of inbox activity
Travel Booking
• Research and present 2–3 flight and hotel options for trips
• Book once I approve — I have specific preferences (detailed in onboarding doc)
• Always prioritize free cancellation
Side Hustle Admin
• Create and send invoices, follow up on payments
• Schedule and publish social media content
• Competitor and market research (summarized, not raw dumps)
• Light website updates
Personal Errands
• Online shopping, returns, gift research
• Booking personal appointments (doctor, salon, etc.)
• Managing home service vendors and logistics

WHAT I’M LOOKING FOR
? Excellent written English — you’ll be managing my inbox
? At least 2 years of VA or executive assistant experience
? Comfortable with Gmail, Google Calendar, and Slack
? Strong attention to detail — especially for travel and scheduling
? Proactive communicator — you update me without being asked
? Reliable internet connection and a dedicated workspace
NICE TO HAVE
• Experience with invoicing tools
• Social media scheduling experience
• Experience supporting a US-based client

HOW WE’LL WORK TOGETHER
• Communication: Slack (primary) — casual, direct, no long reports needed
• Hours: Fully async — work when it suits you as long as tasks are completed on time
• I’ll provide a detailed VA Playbook on day one covering all my preferences
• We’ll do a short check-in call when you start, then run mostly async

HOW TO APPLY
Please do NOT send a generic application. I read every message personally.
To apply, send me:
1. 2–3 sentences on why this role is a good fit for you specifically
2. One example of a task you’ve handled for a previous client that’s similar to this work
3. Your availability and current workload (how many other clients are you supporting?)
4. Your rate
Applications that don’t follow this format will not be reviewed. Looking forward to hearing from you!