Personal Executive Assistant

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. This is not a typical EA role. 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 Responsibilities Daily MLS & Deal Sourcing • 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 • 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 • 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 • Draft and send emails directly on the principal's behalf with accuracy and the right tone • Stay on top of active deal communications, ensuring nothing slips through the cracks Phone Calls on the Principal's Behalf • Make phone calls to agents, vendors, contractors, title companies, and other parties on the principal's behalf • Represent the principal professionally and clearly — strong, professional spoken English is essential for this function • Gather information, confirm details, and follow up on action items from these calls Payroll Management (simple process) • 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 • Flag discrepancies, unusual transactions, or items needing attention quickly • Maintain a sharp, consistent eye on the day-to-day financial pulse of the business Family & Personal Support • Provide full personal support to the principal's wife for anything she needs — business or personal • 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 • Serve as the connective glue across multiple companies, keeping operations running smoothly day to day • Take initiative on tasks and projects that fall outside a defined category — this role will require flexibility and ownership • Identify and solve small operational problems before they become big ones Most Important Qualities • Extremely detailed and organized — this is the single most important quality for this role, full stop • Great with math and numbers — sharp, accurate, and comfortable working with figures every single day • Great personality and easy to work with — this person will be in close daily contact with the principal • Looking for a long-term home — someone who wants to build a multi-year relationship, not a short-term placement • Strong English, written and spoken — professional enough to represent the principal directly on the phone • Fast learner — the principal will be teaching extensively, and this person needs to absorb it quickly and run with it • Comfortable with Claude and other AI tools — the business leans on AI heavily; prior experience is ideal, fast learners are acceptable • Trustworthy and discreet — this person will have access to financials, payroll, and personal and family matters • Proactive self-starter — anticipates what is needed without being told Required Qualifications • 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 • Strong numerical accuracy — comfortable with payroll, financial review, and transaction-level detail • Excellent written and spoken English — professional enough to handle calls with agents, vendors, and contractors • Demonstrated reliability and discretion in past roles, particularly with sensitive financial or personal information • Self-directed and reliable in a fully remote environment Preferred Qualifications • 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 This is a full time role Up to $6/hr 100% Remote