Executive Assistant - Real Estate and Other Business

ABOUT THE ROLE

I am looking for a sharp, adaptable, and highly organized Executive Assistant to support a busy San Diego entrepreneur across three active businesses ->

Commercial real estate brokerage

Golf cart rental company

Two Airbnb properties

Various personal tasks/errands.

This is not a traditional single-role job. You’ll be a right-hand generalist who can shift between coordinating a vendor call, sending a lease document, responding to a guest inquiry, and handling personal logistics - sometimes all in the same day.

*RESOURCEFULNESS* The ideal candidate doesn’t need a playbook or micro-managing.

When given a task, you are able to figure out how to achieve it. You won’t be told which platform to use, which vendor to call, or how to structure your day. You’ll be told what outcome is needed. You have the freedom to operate in a way you deem best. If you need detailed instructions to complete unfamiliar tasks, this role is not a good fit.

WHAT YOU’LL BE DOING

High-End Street-Legal Golf Cart Rentals/Shuttles (Rec Rentals)

• Answer customer calls and send online reservations
• Coordinate maintenance vendors and source parts for fleet of 11 carts
• During downtime, help with sales, marketing ads, registrations, test driving carts, etc.

Short-Term Rentals (Airbnb)

• Manage two active listings — pricing, calendar, photos, reviews
• Coordinate cleaners, restock supplies, oversee property upkeep
• Guest communication pre/during/post stay
• Ondemand: Schedule pest control, generator maintenance, plumbing issues, etc.

Commercial Real Estate Support (Kidder Mathews)

• Support prospecting outreach and follow-up cadences
• LinkedIn management and marketing tasks
• Organize transaction files and legal documents
• Schedule tours, client communications, light research

Personal & Life Operations

• Help with my boat repairs, vendors, parts, etc.
• Errands such as dry cleaning, amazon returns, or taking photos of office buildings
• Car repairs, calendar management, personal task tracking
• A secret business is currently being built in the health and wellness space (TBA)

YOU’RE A GREAT FIT IF YOU…

• Have been called “the person who just handles it” — by multiple employers or people in your life
• When given an unfamiliar task, your first instinct is to research and execute — not ask for a walkthrough
• YOU MUST be utilizing AI, Google, YouTube, and your network as your first line of problem-solving
• Have independently built systems, found vendors, or solved problems with zero prior training in that area
• Are comfortable being evaluated on outcomes, not hours or activity
• Communicate clearly and promptly - multiple check-in calls/week
• Plus: Experience as a personal assistant, executive assistant, or ops coordinator
• Are based in San Diego with a valid driver’s license and reliable transportation
• Are trustworthy with sensitive business and personal information
• Airbnb, property management, or small business experience is a plus — not required

THIS ROLE IS NOT FOR YOU IF…

• You need step-by-step instructions to tackle new or unfamiliar tasks
• You prefer a clearly defined, repetitive job scope
• You wait to be told how before you start
• You need frequent reassurance beyond a scheduled daily check-in
• You’ve thrived in heavily managed environments and struggled when working independently

WHY THIS ROLE IS DIFFERENT

You won’t be bored. No day will be the same. You won’t be siloed. You are someone who has always wanted to learn how multiple businesses actually run and can operate on your own energy. You can pull yourself - no need for me to push.

The right person will grow with this role significantly. Equity is potential. Lots of employee perks, trips, etc. when performance is achieved. You should be making $100k+ by years 2 or 3 if goals are hit. And I hit goals.

I AM LOOKING FOR A LONG-TERM PARTNER - not someone who will learn and then start their own business a year later.

This role is 80% remote. 20% will be on the road, office for short meetings, errands, tours, etc. Disregard the address in the listing.

The compensation is only BASE PAY… There will be BONUSES upon successful real estate transactions, golf cart sales, and other goal accomplishments. I am very much supportive to share in the “wins”!!!

Job Types: Full-time, Part-time

Pay: $20.00 - $29.00 per hour

Benefits:

• Paid time off
• Professional development assistance

Work Location…