Executive Assistant

About Us

A Squared Investments is a U.S. real estate investment company. We buy houses, land, and mobile homes directly from sellers across South Carolina and California. We renovate and resell some of them, sell others to cash buyers, and hold a portfolio of rentals. We also operate a second business in medical equipment sales serving physician practices in the same region.

We are a small, fast-moving team. Everyone here owns outcomes, not just tasks.

The Role

This is an Executive Assistant position supporting the owners of the business — both professionally and personally. You will work directly with the CEO and his wife, who is also his business partner. You will know what is on their plate before they tell you, and you will clear as much of it as possible.

Two things matter more than anything else in this role: you are a self-starter, and you think independently.

We are not looking for someone who waits for a task list. We are looking for someone who sees what needs doing and does it, who brings us solutions instead of questions, and who can be handed something unfamiliar and figure it out. If you need to be told the next step every time, this will be frustrating for both of us.

This is not a cold calling job. We already have a team handling seller conversations.

What You Will Do
Business Support

Property Research

Look up property records, ownership, zoning, tax information, and recorded documents through county and public websites
Research flood zones, land use questions, and utility availability
Gather and organize comparable sales data, and flag anything that looks inaccurate before it reaches us
Verify that property files and photos are complete and correctly organized
Prepare clean, concise research summaries so we can make decisions quickly

Transaction Coordination

Maintain a checklist for every property under contract
Track inspection periods, due diligence windows, and closing dates, and give us early warning before anything is at risk
Follow up with title companies, attorneys, lenders, contractors, and insurance agents until we have what we need
Review closing documents against what we expected and flag any discrepancy, no matter how small
Collect, name, and file signed documents where they belong

Marketing & Buyer Support

Build and maintain buyer and prospect lists using our research tools
Prepare and send email campaigns, then report on results
Keep buyer preferences and criteria recorded in our CRM after every conversation
Assemble property marketing materials from information we provide

Property Management

Field calls from tenants, determine the issues and find the appropriate resource to resolve the situation whether it be a maintenance repair or an administrative task. Process tenant applications and screening, post and respond to openings on vacant units. handle evictions etc.

CRM & Reporting

Keep our CRM clean and current — no duplicates, no missing information, no stale records
Deliver a weekly summary of key numbers across the business
Flag leads and deals that have gone quiet so our team can act Monitor the CEO's mailbox to flag anything that needs his immediate attention.

Medical Sales Support

Build targeted contact lists for physician outreach
Load and schedule email campaigns, monitor responses, and route interested contacts to our sales lead
Follow up on paperwork and orders with our supplier
Executive Support
Calendar and schedule management across business and personal commitments
Inbox triage — sorting what matters, drafting replies, and surfacing what needs a decision
Travel planning and booking, including itineraries and confirmations
Preparing documents, agreements, spreadsheets, and reports
Expense tracking, receipt organization, and light bookkeeping support
Research on vendors, services, tools, contractors, or anything else we are evaluating
Coordinating with team members, vendors, and partners on our behalf
Meeting preparation, notes, and follow-up on action items
Personal Support

This role includes personal and household assistance for the owners and their family. It is a real part of the job, not an occasional favor. Expect things like:

Managing family calendars, appointments, and reminders
Scheduling and coordinating with home vendors, service providers, and contractors
Online ordering, returns, and tracking purchases
Researching and booking personal travel, reservations, and events
Organizing personal documents, records, and subscriptions
Handling accounts, renewals, insurance, and utilities for personal properties
Research on personal decisions, purchases, and services we are considering
Whatever else comes up that we do not have time to handle ourselves

Some weeks the business work will dominate. Other weeks the personal side will. You need to be comfortable moving between the two without treating either as less important. Discretion is essential — you will see personal and financial information, and we need to trust you completely with it.

How We Will Measure You

You will be evaluated on results, not hours logged:

No missed deadlines. No inspection period, due diligence date, or closing date is ever missed because it was not tracked.
Closing files complete well before closing day. Not the morning of.
Buyer criteria recorded promptly after every conversation, every time.
Research turned around within one business day.
Weekly reporting delivered on schedule without being asked.
CRM accuracy that holds up to spot checks.
Requests acknowledged same day and either completed or given a clear timeline.
Problems brought to us with a recommendation attached, not just a description of the problem.
Who We Are Looking For

Required

Fluent written English — you will be email ing U.S. title companies, attorneys, and vendors, and your writing needs to be professional enough that they cannot tell you are not in our office
Strong spoken English for calls with our team and outside parties
At least two years of remote work experience supporting a U.S. company, ideally as an assistant to an owner or executive
Comfortable with spreadsheets, web-based software, and learning new tools quickly
Reliable high-speed internet with a backup option, a working computer, and a quiet place to work
Able to work U.S. Eastern business hours — our vendors and title companies are only reachable during their business day, and we cannot compromise on this
Complete discretion with confidential business and personal information

Preferred

Prior experience in U.S. real estate — transaction coordination, title, escrow, property management, or investor support
Experience with real estate CRMs, property data tools, or email marketing platforms
Comfort reading U.S. purchase contracts and closing documents

The kind of person who does well here

You start things. You notice what needs doing and handle it before anyone asks.
You think for yourself. Given an unfamiliar problem, you research it, form a view, and come to us with a recommendation rather than an open question.
You use judgment. You know which decisions are yours to make and which ones need us, and you rarely get that line wrong.
You are bothered by an inconsistency until you resolve it
You tell us when you made a mistake, immediately, before we find it
You take a process you were taught and improve it, then write down the improvement
You can shift from detailed research to a last-minute personal request without losing the thread on either
You are steady and consistent rather than dramatic and heroic

This job is not for you if you need constant supervision, you want a fixed and predictable task list, you would feel that personal and household tasks are beneath you, you dislike detailed work, or you are looking for something to fill gaps between other clients.

Compensation & Growth
Starting pay: $1,200 – $2,000 USD per month, full-time, depending on experience
Performance review at 90 days with a pay increase for meeting expectations
Paid U.S. holidays and paid time off after 90 days
13th month pay where customary
Annual raises based on performance
Paid monthly via Wise

We are building a long-term team. The person in this role will help shape how we hire and train everyone who comes after them, and there is a clear path into a senior operations position as we grow.

Hiring Process
Application — see instructions below
Written screening questions sent by email
Video interview with our founder
Reference checks with previous supervisors
Offer

We move quickly. Expect about two weeks start to finish.

How to Apply

Send your application with the subject line "Executive Assistant — [Your Name]" and include:

Your resume
A short paragraph, no more than five sentences, describing something you took on for a previous employer that nobody asked you to do
Your available working hours in U.S. Eastern Time

Applications missing any of these three items will not be reviewed. We are testing whether you follow detailed instructions, because that is most of this job.