Role: Executive Assistant to Real Estate Investor / Educator
Location: Remote (U.S.-based preferred)
Type: Independent Contractor
Commitment: ~30 hrs/week (ramping up gradually), 1-year minimum commitment
Overview
We are seeking a highly organized, resourceful, and tech-savvy Executive Assistant to support a busy real estate professional with multiple short- and mid-term rental properties across six states. This role blends property management, administrative support, and community engagement, and is ideal for someone who thrives in a fast-paced, entrepreneurial environment.
The ideal candidate has experience managing short-term rentals, is systems-minded, responsive, and enjoys building and optimizing operational workflows. Strong communication and follow-through are essential, especially in guest communication, vendor coordination, and lead tracking.
Key Responsibilities
Property Management Support
- Create and market property listings across platforms (Hospitable, Furnished Finder, Zillow, etc.)
- Manage guest/tenant communications via text, email, and listing platforms
- Prepare leases, collect deposits, and ensure smooth onboarding
- Schedule cleanings, maintenance, and supply orders
- Coordinate with handymen, contractors, and service providers
- Maintain vendor relationships and act as main point of contact
- Perform basic spreadsheet-based bookkeeping and organization
Administrative Support
- Manage calendar, appointments, and scheduling
- Sort and respond to emails professionally and promptly
- Attend 3x weekly prioritization meetings with principal
- Track and pay invoices, manage accounts payable/receivable
- Streamline internal systems and organize documents
- Track and follow up on leads (intro emails, CRM, campaigns)
- Occasionally assist with personal tasks or one-off projects
- Help launch programs or manage one-time initiatives (e.g., ordering furniture for a property, setting up affiliate programs)
- Train additional staff if/when hired
Community & Marketing Support
- Generate leads via social media engagement (DMs, comments on FB, IG, TikTok)
- Track outreach and responses using internal systems
- Assist with planning and promoting community events (e.g., meetups, workshops, etc.)
- Coordinate with speakers and manage attendee tracking
Key Skills & Attributes
- Excellent written and verbal communication
- Highly organized and detail-oriented
- Strong systems thinking; skilled in optimizing workflows
- Fast and reliable response time (within 1 hour for guest messages)
- Curious and self-driven; enjoys figuring things out independently
- Tech-savvy; eager to learn new tools and platforms
- Creative and resourceful problem-solver
- Experience with copywriting and/or Canva is a plus
- Property management experience is a strong plus
Tools & Platforms You May Use
- Hospitable, Furnished Finder, Zillow
- Google Suite, Slack, Zoom
- Social media platforms (IG, FB, TikTok)
- Canva, Zapier, Calendly
- CRM, email campaign tools (e.g., ConvertKit or similar)
Term & Growth
- Starts part-time (10-20 hrs/week) and scales up to ~30 hrs/week
- Long-term role with potential for growth and additional responsibility
- Ideal for someone seeking a meaningful partnership and willing to grow into a key support role