Personal Executive Assistant

United StatesRemote

Responsibilities

Maintain a consistent, disciplined daily process so no qualifying deal is missed
Track sourced properties, offer status, and deal pipeline activity in an organized system Calendar, Scheduling & Planning
Manage calendar, scheduling, and planning for the principal and his team across multiple companies
Coordinate meetings, calls, and appointments while protecting time for high-priority deal activity
Draft and send emails directly on the principal's behalf with accuracy and the right tone
Make phone calls to agents, vendors, contractors, title companies, and other parties on the principal's behalf
Run and manage payroll across multiple companies accurately and on schedule
Ensure payroll calculations, deductions, and disbursements are correct every cycle
Maintain organized payroll records and resolve any discrepancies promptly Daily Financial Review (simple process)
Review financial transactions daily across the businesses
Coordinate closely with the Bookkeeper, to ensure books stay accurate and current
Maintain a sharp, consistent eye on the day-to-day financial pulse of the business Family & Personal Support
Handle travel planning for the principal and his family, including itineraries and logistics
Manage personal tasks and errands as needed with the same care and discretion applied to business matters General Operations
Identify and solve small operational problems before they become big ones Most Important Qualities

Comfortable with Claude and other AI tools — the business leans on AI heavily; prior
experience as an Executive Assistant, Personal Assistant, or in a comparable high-trust support role
Comfortable working with Gmail / Google Workspace, Excel or Google Sheets, and ClickUp as the team's central hub
Experience in real estate, property investment, or real estate development support
Familiarity with MLS systems and property research
Experience running payroll or supporting a bookkeeping/accounting function Prior
experience using Claude, ChatGPT, or other AI tools in a business support context
Experience supporting a principal across multiple companies or business entities simultaneously

Position Overview We are looking for a Personal Executive Assistant to become a true right hand — working directly with the principal every day across multiple companies, with a heavy emphasis on the real estate and development side of the business.
This person will also be fully available to the principal's wife for anything she needs, business or personal.
The principal will be teaching his systems, workflows, and decision-making directly — which means we need someone who is genuinely excited to learn deeply, grow into the role over years, and eventually operate with real autonomy.
This is a long-term position for someone looking to build a career-defining partnership, not a stepping stone.
The single most important quality for this role is being extremely detailed and organized.
Beyond that, this person needs to be sharp with numbers, easy to work with on a daily basis, and completely trustworthy with sensitive financial, business, and personal information. Core
Scour new MLS listings every single day, filtering against the established buy box criteria
Surface qualified properties for the principal to review and make offers on
Proactively resolve scheduling conflicts and keep the principal's day organized and on track Email & Communications
Triage the principal's inbox daily, prioritizing deal flow, time-sensitive items, and important relationships