About the Role
We own and operate three hotels, a short-term rental (Airbnb) property, and an active house-flipping business, with plans to continue expanding our real estate portfolio and brand. We are looking for a dependable, in-person Operations & Executive Assistant to take ownership of day-to-day coordination across these businesses — freeing up ownership to focus on growth, deal sourcing, and strategic decisions.
This role is not just about completing tasks — it is about building better ways of operating. You will be expected to actively create, organize, and improve systems, maintain a clear and prioritized backlog of ongoing work, and take initiative in solving problems before they become bottlenecks. The goal is to continuously make the business run faster, cleaner, and more efficiently over time.
The role begins with a defined scope, but is designed to expand as you demonstrate reliability, judgment, and the ability to handle more sensitive responsibilities (financial information, vendor relationships, guest and tenant communication).
Executive & Administrative Support
- Manage and respond to the owner's email inbox; flag and escalate anything that needs the owner's decision rather than handling it solo.
- Handle the steady stream of ad hoc tasks and requests that come up throughout the day.
- Build and maintain structured tasks and project backlog
- Support hiring logistics for other roles (cleaners, contractors, vendors) — scheduling interviews, coordinating communication, and tracking candidates.
House Flip & Rental Property Operations
- Monitor and respond to messages in Avail; escalate anything requiring the owner's input or decision.
- Help bring structure and organization to house flipping operations (tracking, conversations, next steps, and open items across contractors, tenants, vendors)
- Ensure follow-ups are happening either on our side, GC side or real estate agent sides
- Own and maintain a key tracking system across all properties — both the physical keys and a digital log of who has what and when.
- Build and maintain a property knowledge base for each property: access codes, vendor and contractor contacts, maintenance history, known issues, and anything future-you would want to remember.
- Create and maintain a centralized file system for property documents — deeds, permits, inspection reports, invoices, warranties — so nothing lives only in someone's inbox or glovebox.
Airbnb Operations
- Respond to guest messages and manage bookings.
- Track and manage inventory and restocking.
- Coordinate scheduling with the cleaning team.
- Manage real-time logistics for late checkouts and early check-ins.
Hotel Support
- Ad-hoc ordering, response management, calendars, etc.
- Pull, organize, and track operational reports and information as requested.
- Help post jobs, phone call interviews
Growth Scope
Flip & Investment Operations
- Data entry and ongoing tracking within our house-flipping software.
- Supporting the sourcing of new investment properties.
- Outreach to real estate agents on the owner's behalf.
Brand & Marketing
- Capturing photo/video content on-site at properties (flips, hotels, Airbnb).
- Supporting social media management and brand-building.
Scaling Support
- Helping document processes and build systems as the portfolio grows.
Pay: From $50,000.00 per year
Benefits:
Experience:
- executive assistance: 1 year (Preferred)
Work Location: Hybrid remote in Burbank, IL 60459
