Remote Executive Assistant

Executive Executive Assistant (Remote, Offshore) — Job Description
Oct 11, 2026 · @Jennifer Green
The role
Full-time remote Executive Assistant, 40 hours a week on US Eastern business hours, paid as an independent contractor. You will support a DC-area property management executive across her calendar, two small Virginia businesses, and family planning.
The businesses are Serendipity, a consulting firm, and Joe's Transportation, a local delivery and freight company launching in 2027. Start date is December 1, 2026.
What you will do
Calendar and scheduling
Own the calendar: scheduling, conflict checks, reminders and a Sunday look-ahead for the week
Keep business deadlines, filings and family events on one shared calendar
Email and communication
Triage two business inboxes daily and send routine replies from approved templates
Draft client, vendor and quote-request emails for approval
Send an end-of-day summary: done, waiting, at risk
Serendipity (consulting)
Capture receipts and draft invoices
Prepare monthly records for the bookkeeper and CPA
Track client follow-ups and proposal deadlines
Joe's Transportation (delivery and freight)
Maintain the licensing and filing tracker: state, DMV, federal and annual renewals
Request and compare insurance, vehicle and vendor quotes
Prepare forms for signature
Online presence
Run the posting calendar for LinkedIn, Facebook, Instagram and Google Business Profiles
Schedule posts in Canva or a scheduling tool and reply to reviews
Family planning and travel
Research and price trips, build itineraries and booking checklists
Track savings milestones and payment due dates
Who decides what
You act on your own in the first column, prepare work for approval in the second, and never handle the third.
Area
You own
You prepare, Jenn approves
Stays with Jenn
Calendar
Scheduling, conflicts, reminders
Declining meetings, moving family events
Priorities
Email
Triage, template replies
Anything to clients, banks or the state
Personal and Ruddy work email
Serendipity
Receipts, invoice drafts, follow-up reminders
Sending invoices and proposals
Bank access, payments
Joe's Transportation
Filing tracker, renewal dates, quote requests
Insurance and licensing forms
Signatures, payments, government portal logins
Online presence
Posting calendar, scheduling, review replies
New content, website edits
Account ownership, passwords
Travel
Price tracking, itineraries
Bookings and deposits
Payment cards

Access comes through delegated mailboxes, shared calendars and a team password manager. You will never hold bank logins or card numbers.
What you bring
Required
3+ years supporting a US-based executive or business owner remotely
Fluent written and spoken English
Strong with Google Workspace, shared calendars and a task tool (Asana, Trello or similar)
Reliable internet, backup power, and a quiet workspace
Available Monday to Friday, 8:00 AM to 5:00 PM US Eastern
Sound judgment with confidential personal and financial information
Nice to have
Bookkeeping basics (QuickBooks or Xero)
Canva and social media scheduling
Experience with US small-business filings or property management
Travel planning for families
Schedule, pay and terms
Item
Detail
Hours
40 per week, Monday to Friday, 8:00 AM to 5:00 PM US Eastern
Pay
About US$1,300 a month (US$7.50/hour), paid monthly through [platform]
Status
Independent contractor
Tools provided
Google Workspace accounts, password manager, task tool
Confidentiality
Signed contractor agreement with confidentiality terms before access is granted
Review
Weekly

How to apply
Send a short note on why this role fits you, your past executive-support experience, and your available start date.
Written application
Two-minute recorded video introduction
Live video interview during US Eastern hours
Paid one-week trial project
Contractor agreement and onboarding, starting immediately