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SMART PERSON WANTED: Executive Assistant | Real Estate, Business Operations, Legal & AI

Bessinger Management Group
Martinsburg, WV Full Time
POSTED ON 10/11/2026
AVAILABLE BEFORE 2/8/2027

No fancy degree required. Common sense, curiosity, and a willingness to figure things out? Absolutely required.

Are you the person everyone calls when they need something solved? The one who can research just about anything, find answers, and somehow make the impossible look manageable?

Maybe you learned more from Google, YouTube, ChatGPT, and real-life experience than you ever did in a classroom. Maybe you enjoy a challenge more than a predictable routine.

If that sounds like you, keep reading.

I own a growing real estate and remodeling business and am looking for a sharp, resourceful, tech-savvy assistant who wants more than just another job.

I need someone who can think independently, take initiative, embrace technology (especially AI), and isn't intimidated by unfamiliar assignments. An interest in legal matters, business operations, and problem-solving is a definite plus.

What You'll Be Doing

Legal Research & Administrative Support

A significant part of this position involves using ChatGPT and other AI tools to research, organize, and prepare information relating to legal and business matters across several states.

Projects may include:

  • Researching court procedures involving civil judgments, collections, wage garnishments, and judgment enforcement.
  • Organizing documentation and preparing case summaries for attorneys.
  • Drafting demand letters, correspondence, and administrative complaints involving businesses, contractors, tenants, and consumer disputes.
  • Researching procedures for manufactured-home titles, property deeds, and real estate transactions.
  • Preparing and organizing documents for court filings and attorney review.
  • Following up with courts, government agencies, creditors, manufacturers, and other businesses.
  • Digitizing, reviewing, and organizing extensive records using AI-assisted tools.
  • Tracking deadlines, outstanding matters, and follow-up responsibilities.

All legal-related assignments are administrative or research-based and performed under appropriate supervision. This is not an attorney position and does not involve providing independent legal advice.

Business Operations & Technology

You'll also assist with a variety of business projects, including:

  • Updating Airbnb and real estate websites.
  • Setting up and organizing online utility and vendor accounts.
  • Researching AI-powered bookkeeping and business management software.
  • Improving communication and meeting systems, including Zoom.
  • Managing Facebook Marketplace purchases and sales.
  • Coordinating with vendors, contractors, customers, and business contacts.
  • Identifying opportunities to improve efficiency through technology and automation.

And yes, there will be projects that aren't on this list. That's part of the fun!

What I'm Looking For

  • AI-savvy: Comfortable using ChatGPT or genuinely excited about becoming highly proficient with AI technology.
  • Resourceful: You don't stop at "I don't know." You start with "Let me figure that out."
  • Organized: Able to manage multiple projects, documents, deadlines, and details.
  • Quick learner: Willing to watch tutorials, research unfamiliar subjects, and develop new skills.
  • Confident communicator: Comfortable speaking with attorneys, businesses, government agencies, and people from all walks of life.
  • Independent thinker: Someone who can take an assignment and run with it without needing step-by-step instructions.
  • Dependable: Trustworthy, professional, discreet, and committed to following through.
  • Curious: Interested in understanding how businesses operate, how deals happen, and how problems get solved.

Experience in real estate, legal administration, business operations, or technology is helpful, but not mandatory.

What You Can Expect

This isn't your typical assistant position, and I won't pretend it is.

One day you might be researching a legal procedure in West Virginia. The next, you could be updating a real estate website, coordinating a property transaction, or figuring out how AI can streamline an entire business process.

You'll receive guidance, mentoring, and opportunities to learn. My approach is straightforward: I'll explain what needs to be accomplished, provide direction, and trust you to use your judgment and resources to get it done.

Will you make mistakes? Probably. We all do. What matters is that you learn, improve, and keep moving forward.

You'll have exposure to real estate, remodeling, business development, technology, and legal administrative processes, with meaningful responsibility and opportunities for advancement.

What's in It for You?

  • Full-time employment with a growing business.
  • Hands-on experience across multiple industries.
  • Opportunities to develop valuable AI and business skills.
  • Direct mentoring and professional development.
  • Variety, independence, and meaningful responsibility.
  • Potential for advancement and performance-based compensation.

Who Should Apply?

Someone who is smart, motivated, adaptable, and genuinely enjoys figuring things out.

You don't need an impressive degree or a picture-perfect resume. You do need a strong work ethic, good judgment, attention to detail, and the ability to follow through.

If you need every day to look the same or every assignment to come with detailed instructions, this probably isn't your dream job.

But if you enjoy challenges, love learning new things, and want to become an important part of a growing business, we should talk.

How to Apply

Submit your resume, but don't stop there and most important:

Provide a summary telling me a little about yourself. What makes you resourceful? Have you used ChatGPT or other AI tools to solve a problem? What's something you figured out on your own that you're proud of?

I want to know how you think, not just where you've worked.

I'm not simply looking to fill a position. I'm looking for the right person to help build something bigger.

Pay: $13.50 - $21.00 per hour

Expected hours: 25.0 – 40.0 per week

Benefits:

  • Flexible schedule

Work Location: Hybrid remote in Martinsburg, WV 25403

Salary : $14 - $21

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