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Executive Assistant (Independent Contractor, Remote) I

September 14, 2026

About the Role Are you a systems thinker who thrives on making order out of chaos? We’re seeking a remote Executive Assistant (Independent Contractor) to support Mel Dorman — a real estate investor, author, and founder of the Seller Financing Academy. This is a flexible, part-time contractor role (~30 hours/week) for a proactive operator who loves creating structure, automations, and communication systems that free up leadership time. About Mel Mel Dorman is a Portland-based entrepreneur and financial activist who helps people build community-centered wealth through creative real estate strategies. She leads a multimillion-dollar portfolio, a national coaching academy, and frequent speaking events — all of which need behind-the-scenes coordination and systems support. Responsibilities You’ll manage Mel’s operational world — inbox, calendar, student communications, and automation systems — with ownership and precision. Executive Support <ul> <li> Manage inbox and calendar: triage, prioritize, draft replies </li> <li> Coordinate meetings, speaking engagements, and podcast appearances </li> <li> Book travel and prepare itineraries </li> <li> Respond to media and partnership requests (bios, photos, etc.) </li> </ul> Systems & Operations <ul> <li> Build and maintain SOPs that improve efficiency </li> <li> Set up automations in HubSpot, Zapier, and OnceHub </li> <li> Draft and schedule newsletters, reminders, and student announcements </li> <li> Track testimonials, affiliate payouts, and digital assets </li> </ul> Seller Financing Academy Support <ul> <li> Onboard new students and manage follow-ups </li> <li> Monitor inbox and student questions, escalate as needed </li> <li> Manage student access, payment plans, and class announcements </li> </ul> Property Management Coordination <ul> <li> Prepare leases and renewals from approved templates </li> <li> Track rent increases and renewal timelines </li> <li> Organize monthly financial documents for bookkeepers </li> </ul> You’re a Great Fit If You ✅ Love creating systems that help visionaries thrive ✅ Are confident writing and communicating in someone else’s voice ✅ Are proactive — you see what needs to be done before being told ✅ Can juggle multiple projects without dropping the details ✅ Care about values-driven business and community impact Required Qualifications <ul> <li> 3+ years of experience as an Executive or Administrative Assistant </li> <li> Proficiency with Google Workspace, HubSpot (or similar CRM), Zapier/Make, ChatGPT, and QuickBooks Online </li> <li> Excellent written communication and attention to detail </li> <li> Comfortable working autonomously and managing confidentiality </li> <li> Located in a time zone that overlaps 9 am–1 pm Pacific </li> </ul> Bonus Points <ul> <li> Background in real estate, coaching, AI automation, or online education </li> <li> Experience supporting thought leaders or course creators </li> <li> Light design or copywriting skills (newsletters, templates) </li> <li> Familiarity with seller financing or community-based entrepreneurship </li> </ul> Contract Details <ul> <li> Independent Contractor (1099) </li> <li> Approx. 30 hrs/week @ $35/hr </li> <li> Flexible schedule within business hours </li> <li> Monthly invoicing; renewable quarterly </li> <li> Long-term partnership potential for the right fit </li> </ul> How to Apply Please complete this short application form: Link <a href="" target="_blank" rel="noopener noreferrer">Here</a> You’ll be asked to: <ol> <li> Share a 2-minute Loom video introducing yourself and a system you’ve built. </li> <li> Describe your email triage process to keep an exec’s inbox under control. </li> <li> Write a 3-sentence reply to a podcast booking request. </li> <li> Share your time zone and preferred working hours. </li> </ol> We’ll reach out to qualified applicants for to arrange interviews. <hr class="lis-container__job__content__description__hr">

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...