Tax Resolution Specialists, Inc.

Executive Assistant to a US Business-Owner Couple | Healthcare & Real Estate | Full-Time US Eastern Hours

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: TYPE OF WORK

Full Time

: SALARY

1000-1400 usd / month

: HOURS PER WEEK

40

: DATE UPDATED

Oct 23, 2026

JOB OVERVIEW

ABOUT THIS ROLE

I'm Ken Allen, an Enrolled Agent with 26 years in US tax. I run a tax advisory firm, and I'm recruiting this role for a client.

My clients are a married couple in the US who own healthcare and real estate businesses. They are busy, successful and buried in admin. They need one sharp, trustworthy person to take it off their plate and keep it off.

You'll work for both of them. You will be contracted and paid by their company, not by my firm. I run the search and the screening. They make the final pick.

THE ROLE

You're their right hand for everything that isn't the core of their businesses.

Inbox and calendar

- Triage both inboxes. Surface what truly needs them, handle the rest
- Run two calendars that overlap: business, family and personal. Catch conflicts before they happen
- Prep them for meetings and calls with what they need to know

Banking and admin

- Call and email banks, insurance companies, vendors and government offices on their behalf. Sit on hold so they don't have to
- Open accounts, chase paperwork, follow up until it's done
- Track subscriptions and recurring charges. Flag what they don't use and what went up

Documents and passwords

- Gather and organize documents, including what their accountant needs each year
- Keep their logins organized in a shared password manager
- Build simple trackers and checklists so nothing falls through the cracks

What you will NOT do: you will never access patient or medical records at their healthcare businesses, and you will never send or approve payments or wires. Bank access starts view-only. Trust and access grow over time.

REQUIRED

- 3+ years as an executive assistant or personal assistant to a US business owner, executive or physician
- Excellent written English. Your emails could pass for a US assistant's
- Clear, confident spoken English. You'll be on the phone with US banks and vendors
- Able to work 9:00 AM to 5:00 PM US Eastern, Monday to Friday, every week
- Full-time only. This is your one job
- Experience with Google Workspace or Microsoft 365, and a password manager (1Password, Bitwarden, LastPass or similar)
- Reliable internet plus backup power and backup internet

STRONG PLUS

- You've supported two bosses at once, or a couple or family
- Healthcare, medical practice or real estate background (admin side)
- You've handled US banking tasks: account openings, document requests, disputes
- You use AI tools to work faster and you check their work

WHO THRIVES HERE

- You'd rather close a loop today than send a reminder tomorrow
- You call when calling is faster
- You ask a good question instead of guessing on things that matter
- You treat private information like it's your own
- You want a long-term home. They're hiring for years, not months

PAY

- $1,000 to $1,400/month based on experience and what you show in the test task
- Paid directly by the couple's company
- Paid test task for shortlisted candidates

HOW TO APPLY

To show me you read this whole post, start your application with the exact phrase: "Off your plate." Applications without it will be skipped, no exceptions.

Then send:

1. Your resume
2. Short answers to these three questions:
- Two requests land at 9:05 AM Eastern. One owner asks you to book a dinner with friends Thursday at 7 PM. The other owner already blocked Thursday evening for both of them for a family event. Neither one is answering messages. What do you do?
- A manager at one of their healthcare businesses emails you a scanned form and asks you to save it to the owners' shared folder. You open it and it's a patient's intake form with a name and diagnosis. What do you do?
- Tell me about a time you took a messy errand off a busy boss's plate and finished it. A bank, insurance company, government office or vendor. What was it, what did you do step by step, and how long did it take?
3. A voice recording or short video, 1 to 2 minutes. Start by leaving a voicemail as if you're calling a US bank for your boss: "Hi, this is [your name], executive assistant to [boss's name]. I'm calling about..." Then introduce yourself in English.

Shortlisted candidates get a few written follow-up questions, a 15-minute video call with me, then a paid test task. The couple meets the finalists.

I read every application myself.

Ken Allen, EA

SKILL REQUIREMENT

Calendar Management Personal Assistant Executive Assistance

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Tax Resolution Specialists, Inc.

Executive Assistant to a US Business-Owner Couple | Healthcare & Real Estate | Full-Time US Eastern Hours

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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