Executive Personal Assistant/Estate Manager

Role Overview

We seek a seasoned Executive Personal Assistant with extensive expertise in property and vendor management. The ideal candidate will work closely with the principal in a shared office setting, fostering a reliable partnership to manage her personal affairs, home projects, and multiple properties effectively. This position demands discretion, thoughtful communication, and professionalism to maintain smooth operations.

Job Scope

The role combines high-level executive and personal assistance with property oversight across four residences located in Washington DC (primary), Michigan, New York, and Massachusetts. The assistant coordinates with staff and vendors at these locations to ensure smooth functioning while providing dedicated one-on-one support to the principal.

Additionally, the assistant will contribute to the principal’s philanthropic initiatives by supporting foundation operations, handling research, managing communications, and organizing special projects.

Working Hours

The position adheres to a stable schedule from Monday to Friday, 9 AM to 5 PM, reflecting the principal's preference for routine and clear work-life boundaries.

Work Environment and Principal Profile

The principal is a Washington DC resident actively engaged in personal, civic, and philanthropic activities who maintains multiple properties with a household support team. She values organization, steadiness, observance, and a structured management style. The ideal assistant respects her preferences, communicates clearly, and offers seamless and aligned support.

Key Responsibilities

• Maintain a calm, professional demeanor in shared workspaces and collaborate directly with the principal daily.
• Serve as the principal’s official representative with family, friends, and colleagues.
• Manage and coordinate the principal’s calendar, meetings, and logistical arrangements.
• Maintain up-to-date contacts, emergency information, and key data repositories.
• Produce written updates and summaries aligned with the principal’s preferred formats.
• Draft correspondence and documentation with precision and excellent penmanship.
• Assist in processing bills and tracking expenses in cooperation with the principal’s wealth manager.
• Handle administrative tasks such as mail management, scanning, filing, and document organization.
• Support research, archival projects, writing tasks, and foundation operations including fundraising coordination.
• Oversee the DC residence staff and vendors, fostering leadership while respecting established workflows.
• Manage property calendars, maintenance plans, contracts, and documentation across all residences.
• Vet, schedule, and supervise vendors, ensuring competitive bidding and quality control.
• Coordinate landscaping, groundskeeping, seasonal maintenance, and pool/hot tub care as necessary.
• Prepare properties for principal and guest visits, ensuring timely readiness.
• Monitor and report on safety and security systems to the principal.
• Manage special property projects, inventory, and organizational improvements.

Requirements

• 7 to 10 years of experience supporting private principals or families in high-touch settings.
• Strong administrative skills in document and filing management (both digital and paper).
• Exceptional written communication with neat penmanship; writing samples are required.
• Advanced proficiency in Apple technology, iCal, spreadsheets, and general office software.
• Proven ability to manage household staff and multiple vendors with diplomacy.
• Comfort working in close physical proximity to a principal daily.
• Ability to uphold strict confidentiality and exercise sound discretion.
• Professional demeanor, solid judgment, and ability to collaborate with a direct personality.

Ideal Candidate Attributes

• Highly organized, perceptive, and quick to understand preferences.
• Composed and unflappable in face of direct communication.
• Enjoys creating structure, managing information flow, and maintaining systems.
• Reliable and trustworthy, committed to building a strong partnership with the principal.
• Capable of managing multiple properties, deadlines, and relationships both locally and remotely.
• Understands and maintains high standards without ego.
• Communicates clearly and succinctly, both verbally and in writing.
• Protects the principal’s privacy with humility and good judgment.
• Spanish language skills are a plus for interaction with staff and vendors.
• Excellent references and a track record of longevity in previous roles are essential.

Compensation and Benefits

• Salary set at $150,000 annually, commensurate with experience.
• Eligible for annual performance bonuses.
• Health insurance coverage provided fully for the employee.
• Thirteen paid holidays per year.
• Ten days of paid time off annually.