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Executive Assistant – Right Hand to a growing Entrepreneur
Overview
Location: Remote (U.S.-based only)
Schedule: Mon–Fri, about 5 hours per day. Flexible but must be between 10am-4pm EST
Pay: Starts at $23/hour, with performance-based increases after 30 days
Type: 1099 Contractor
Start Date: ASAP
👋 About Me & This Role
I’m a founder/entrepreneur running multiple real estate businesses:
– A portfolio of short-term rental (STR) properties we own & manage
– A real estate acquisitions company focused on finding off-market deals to buy or flip
– A flat rate co-hosting business –just launched this an focusing on growth
You don’t need to have knowledge or experience in these industries. All three businesses are growing—and I’m at the point where I need someone to step in as my right hand. This is not just another virtual assistant role. It’s a unique opportunity to become deeply embedded in how a founder thinks, operates, and scales multiple companies.
I’m looking for someone sharp, reliable, and proactive—someone who can keep me organized, manage small but important tasks, and make sure nothing falls through the cracks. You’ll learn a lot about real estate investing, operations, and how to run a lean business. Over time, this role has room to grow in both responsibility and compensation.
You’ll also support light personal tasks for my wife and me. Think of this as a true right-hand role—where anything that supports the business or our life is fair game. Nothing is “beneath you” if it keeps us moving forward.
My goal for this role is to essentially download my brain to you on a high level – so you understand the big picture of everything I am working on in order to support the big goals and keep me on track too.
Organization, attention to detail, and follow through are key traits you must have. I need to be able to mention an outcome I desire and trust that you are working to make it happen without me having to remind or circle back. I’m happy to give input along the way, train, and help you grow your knowledge and skills to succeed.
🧠 Your Responsibilities
• Operations Coordination
• Monitor weekly maintenance issues and invoices
• Help manage STR listing updates (photos, pricing, descriptions)
• Track and follow up on open tasks (especially delegated to VAs)
• Maintain ClickUp boards and make sure things don’t stall
• Founder Enablement
• Keep my calendar, inbox, and weekly focus tight and intentional
• Remind me of priorities and help me stay on track
• Handle recurring or one-off business tasks
• Own outcomes—I should never need to chase you for follow-through
• Team Communication
• Coordinate and oversee the work of our virtual assistants (they are the main day to day property mangers for the STR properties)
• Keep SOPs and checklists up to date
• Make sure small details don’t become big problems
• Personal Support
• Light logistics or errands (e.g., scheduling appointments, booking travel)
• Helping manage to-dos for me or my wife as needed
🧩 You Might Be a Great Fit If…
• You take pride in follow-through and don’t need reminders
• You love organizing chaos into clear next steps
• You’re curious about real estate or business and love to learn
• You’re comfortable juggling a variety of tasks and contexts
• You’re the kind of person people rely on and trust with details
• You want to grow into a long-term, high-trust role—not just pick up hours
🧰 Tools You’ll Use (or Learn Quickly)
• Google Workspace (Docs, Sheets, Gmail, Calendar)
• ClickUp
• Loom
• STR tools like OwnerRez, Hospitable (easy to train on)
💲 Compensation & Growth
Starting Pay: $23/hour for the first 30 days (25 hours/week)
After 30 Days: Performance-based raise to $25–28/hour
Growth Path: Long-term opportunity to increase hours, pay, and ownership
Potential to grow into an operations or integrator-type role if the fit is right
📩 How to Apply
Send an email to ops@STRsuccessteam.com with:
1. A brief intro: Who you are and why this role excites you
2. A link to your resume
3. A video (use loom.com or any other tool you want) describing your past experience
4. Use subject line: “Executive Assistant Application – [Your Name]”
💬 Final Thought
This is more than a part-time assistant role. It’s a chance to plug into the inner workings of growing businesses, be the steady hand behind the scenes, and learn directly from a founder. If you’re looking for a flexible, meaningful, long-term role where your reliability and ownership mindset will shine—I’d love to hear from you.