Personal Assistant / Estate Manager

Salary: $160,000 to $170,000 plus bonus and healthcare stipend

Location: Remote. Should live near NYC and or CT. Occasional Connecticut and New York with travel between residences

Schedule: Monday through Friday with flexibility and occasional off hours

A warm, down to earth, friendly family looking for a seasoned professional who can operate as a true personal assistant while helping manage the day to day flow of a few private homes.

This role requires someone who plans ahead but can adjust quickly when things change. Calm, organized, and steady is key. Must be highly tech savvy and comfortable taking full ownership of calendars, scheduling, and anything digital. You will be working with someone who is not implemented tech solutions that would be beneficial for the running of the household but would like to. You need to stay on top of it and keep things moving without hand holding. This is a hands-on role for someone who understands how a home actually runs and does not get rattled when priorities shift.

Overview

This position supports a private family across multiple homes with a mix of personal assistant responsibilities and household management. The right person brings structure, discretion, and sound judgment. Proactive, detail oriented, and comfortable managing both people and process.

Key Traits

Highly organized with strong follow through

Calm under pressure and able to shift gears quickly

Proactive thinker who anticipates needs

Discreet and trustworthy

Strong communicator

Strong EQ. Reads people well and knows how to respond

Strong team player. Steps in and takes the lead when needed

Tech savvy. Manages electronic calendars, appointments, and scheduling

Responsibilities

Household and Property Oversight

Oversee day to day operations across multiple homes

Coordinate vendors, contractors, and service providers

Schedule and track maintenance and repairs

Act as point person for ongoing projects, including design and household needs

Maintain organized systems for the home including storage, inventories, and service logs

Handle basic troubleshooting and coordinate outside support when needed

Personal Assistant Support

Manage electronic calendars, appointments, and scheduling

Coordinate travel including flights, ground transport, lodging, and itineraries

Plan events such as holidays, dinners, and family gatherings

Handle gifting, reminders, and personal details

Organize documents, records, and household information

Assist with errands, sourcing, and day to day needs

Conduct research and provide summaries when needed

Additional Support

Coordinate logistics related to extended family as needed

Help manage appointments and transportation when required

Support communication between homes, vendors, and any existing staff

Compensation and Structure

Salary range: $160,000 to $170,000 based on experience

Performance Bonus: approximately 10 percent

Healthcare stipend: $500 per month or more depending on structure

Mileage or travel reimbursement for property visits

Two weeks vacation with flexibility on both sides based on schedule and needs