Executive Personal Assistant

Senior Personal Assistant & Principal Operations Lead

New York City (Primary Residence) + Secondary Property (2–3 Hours from NYC)

Full-Time | Core hours approximately 9:00am–6:00pm with flexibility and on-call responsiveness as needed

Compensation: Up to $200,000 base DOE + benefits stipend + additional perks

A private principal with substantial business, investment, and real estate interests is seeking an exceptional Senior Personal Assistant & Operations Lead to serve as a true right hand. This is a high-trust, highly visible role supporting a principal whose responsibilities extend far beyond a traditional 9–5 business.

This position blends personal support, operational oversight, and business-adjacent coordination, requiring someone who naturally thinks in systems, workflows, and accountability. The ideal candidate is detail-driven, highly organized, and comfortable acting as the connective tissue across multiple priorities, properties, and professional teams.

The principal is warm, respectful, and collaborative, yet operates with an exacting standard and fast-moving pace. Precision, follow-through, and anticipation are essential.

The role is based primarily in New York City, with regular time spent at a secondary residence approximately 2–3 hours outside the city. When on-site, private accommodations are provided.

Key Responsibilities

Principal Support & Daily Operations

• Serve as a true right hand to the principal, managing priorities, tracking details, and ensuring seamless execution across all areas of responsibility
• Prepare daily and forward-looking agendas; maintain clear tracking of action items, deadlines, approvals, and follow-ups
• Provide real-time personal support throughout the day, adapting fluidly to shifting priorities and emerging needs
• Manage sensitive communications with discretion, professionalism, and strong emotional intelligence

Business-Adjacent & Operational Coordination

• Partner closely with the business Chief of Staff and Executive Assistant to ensure alignment between personal, operational, and business priorities
• Monitor and manage task flow across platforms such as Asana, ensuring all open items, projects, and follow-ups are actively tracked and closed
• Interface with internal and external stakeholders including CFO, accountants, investment partners, legal teams, and representatives tied to the principal's various ventures
• Support investment, philanthropic, and special projects by tracking documentation, approvals, reporting needs, and next steps

Financial & Administrative Oversight

• Review and monitor daily to ensure expenses, approvals, and payments remain current and accurate
• Liaise with financial partners to support expense tracking, bill pay, reporting, and documentation across multiple entities and properties
• Maintain organized records for insurance, vehicles, warranties, registrations, and other critical documentation

Real Estate & Asset Oversight

• Oversee operational needs across multiple residences, ensuring properties are consistently staffed, maintained, and prepared
• Manage ongoing property punch lists, tracking repairs, maintenance, approvals, and completion timelines
• Coordinate with vendors, contractors, designers, and service providers; escalate decisions thoughtfully and efficiently
• Provide light renovation and project oversight by fielding day-to-day questions and maintaining momentum on active initiatives

Travel, Logistics & Personal Support for

• Coordinate travel logistics in partnership with the Executive Assistant, ensuring preferences, schedules, and contingencies are accounted for
• Manage family logistics including medical appointments, reservations, gifting, special occasions, and guest coordination
• Serve as point of contact for short-term or seasonal renters at one residence
• Oversee care coordination for the family's dogs, including scheduling and in-home support during travel
• Act as a safe, reliable driver when needed

Ideal Candidate Profile

• Exceptionally organized; comfortable living inside systems, task trackers, and financial workflows
• Strong judgment, discretion, and emotional intelligence
• Confident interfacing with senior-level stakeholders and professional teams
• MUST know and or can learn ASANA
• Proactive, solution-oriented, and comfortable operating with autonomy
• Flexible, adaptable, and willing to stay on property as needed
• Valid driver's license and clean driving record
• Extensive Background Check