Executive Personal Assistant

ABOUT THE PRINCIPALS

You will be supporting two principals — a husband and wife — whose combined professional and personal lives span a broad range of industries and activities:

• Multi-industry professional and entrepreneurial endeavors across finance, entrepreneurship, and business operations
• Active AI ventures and technology-driven businesses requiring fast-moving operational support
• A deep commitment to philanthropy, with ongoing charitable initiatives, donor relationships, and community engagement that require thoughtful coordination and support
• Three or more residences requiring ongoing coordination across property managers, vendors, and household contacts
• Extended family relationships and occasional family logistics that require thoughtful, discreet management
• Frequent domestic and international travel, including both planned itineraries and last-minute changes
• A broad network of advisors, partners, vendors, and personal contacts globally

This role will require someone who is not only highly organized and discreet, but who brings intellectual curiosity, emotional intelligence, and a deep commitment to excellence across everything they touch.

OVERVIEW

We are seeking an exceptional Executive & Personal Assistant to serve as a trusted right hand to two principals in a sophisticated family office environment. This is a high-trust, high-touch role spanning executive support, personal assistance, household coordination, travel, scheduling, and day-to-day logistics across both professional and personal lives — simultaneously, and at a consistently high standard.

The ideal candidate is polished, highly organized, discreet, and calm under pressure. They are equally comfortable managing complex calendars, coordinating international travel, handling sensitive personal matters, drafting correspondence, overseeing follow-through, and bringing order to a fast-moving environment with many competing priorities. They have excellent judgment, strong interpersonal instincts, and a natural ability to anticipate needs before they arise.

A meaningful part of this role is the intelligent use of AI tools and agentic workflows. We are looking for someone who does not simply work harder, but works smarter — someone who is eager and able to automate recurring tasks, streamline coordination, improve responsiveness, and build lightweight systems that make support more efficient, reliable, and scalable.

This position requires excellent judgment, a no-drama mindset, and a genuine commitment to making two demanding lives run seamlessly.

Important Note on Availability: This role requires high availability throughout the day, including evenings and weekends. The Principals operate across time zones, travel frequently, and require a level of responsiveness commensurate with their pace. Candidates who require strictly defined hours should consider whether this is the right fit.

RESPONSIBILITIES

Executive & Personal Support

• Manage and coordinate calendars for both principals across business, personal, family, social, and travel commitments
• Balance overlapping priorities, shifting schedules, and last-minute requests across two principals with efficiency and diplomacy
• Coordinate meetings, appointments, reservations, and daily logistics for both principals, individually and jointly
• Anticipate needs in advance and ensure both principals are always prepared, informed, and well supported
• Help manage inbound requests and competing demands on time and attention across multiple businesses and personal obligations
• Handle a broad range of personal assistant responsibilities with responsiveness, professionalism, and absolute discretion

Travel, Family & Lifestyle Logistics

• Arrange detailed domestic and international travel, including private and commercial flights, hotels, ground transportation, dining, itineraries, and last-minute changes
• Coordinate across three or more properties: manage schedules with property managers, household vendors, service providers, and maintenance contacts
• Coordinate family logistics including important dates, celebrations, gifting, appointments, and extended family obligations as needed
• Assist with lifestyle management including purchases, deliveries, returns, household scheduling, and special requests
• Ensure logistics across home, family, and travel are handled smoothly, proactively, and without the principals having to ask twice
• Coordinate with household staff, service providers, vendors, and outside contacts as needed across all residences

Communication & Administrative Coordination

• Draft, edit, proofread, and manage emails, letters, and other written correspondence on behalf of both principals
• Track follow-ups, reminders, and action items to ensure nothing is missed across business and personal domains
• Prepare agendas, briefing notes, summaries, and other support materials as needed
• Maintain organized records, contacts, files, and important documents across business and personal matters
• Handle scheduling outreach, confirmations, calls, and routine coordination with polish and professionalism
• Build and maintain clear administrative systems that are accurate, current, and easy for both principals to navigate

HR, Payroll & Vendor Management

• Manage payroll processing and coordination with the principals’ accountants and payroll providers for household and personal staff
• Maintain organized HR records for any household or personal employees, including onboarding documentation, schedules, and personnel files
• Liaise with benefits providers, insurance contacts, and external HR or accounting advisors as needed
• Coordinate contracts, invoices, and payments for vendors, service providers, and recurring household expenses
• Track and reconcile household and personal expenses, supporting the principals’ financial team with accurate records

AI, Automation & Workflow Optimization

• Use AI tools and agentic workflows to automate as much of the role as practical while maintaining quality, judgment, and confidentiality
• Build systems for scheduling, reminders, drafting, follow-ups, travel planning, information retrieval, and recurring administrative work
• Identify repetitive tasks and redesign them into more efficient workflows using tools such as Claude, ChatGPT, task automation platforms, and related technologies
• Create lightweight systems for organization, task tracking, contact management, and document management across both principals
• Continuously evaluate new AI tools and automation opportunities that can improve speed, consistency, responsiveness, and leverage
• Apply technology thoughtfully to reduce manual work and increase efficiency across professional and personal life

Trusted Right Hand Support

• Serve as a reliable, composed, and highly trustworthy extension of the principals at all times
• Navigate the preferences, communication styles, and evolving priorities of two distinct principals with maturity and good judgment
• Build strong working relationships with advisors, household contacts, vendors, family contacts, and other key external parties
• Handle all sensitive information with absolute discretion
• Bring a calm, resourceful, solutions-oriented approach to both routine responsibilities and unexpected changes
• Represent the principals with professionalism and warmth in all interactions with third parties

QUALIFICATIONS

Required

• 5+ years of experience in a high-level Executive Assistant, Personal Assistant, or similar role
• Significant experience supporting a senior executive, founder, principal, or entrepreneur in a demanding, fast-moving environment
• Proven experience supporting multiple stakeholders or principals simultaneously
• Exceptional organizational skills and meticulous attention to detail across business and personal domains
• Proven ability to manage complex calendars, international travel, scheduling, and logistics at a high level
• Excellent written and verbal communication skills; able to draft polished correspondence independently
• Strong judgment, professionalism, and discretion — especially in high-stakes or sensitive situations
• High level of initiative and ability to work independently with minimal direction
• Comfort handling both executive support and deeply personal assistant responsibilities simultaneously
• Advanced proficiency with Google Workspace, Microsoft Office, and standard productivity tools
• Strong fluency with AI tools and agentic workflows, with demonstrated ability to apply them in practical day-to-day operations
• Willingness to sign a Non-Disclosure Agreement prior to commencement of employment

Preferred

• Experience in a family office, private office, or high-profile principal environment
• Experience coordinating across multiple residences, household staff, and property vendors
• Familiarity with New York City logistics, travel, dining, and service networks
• Experience with Notion, Airtable, Zapier, n8n, or similar workflow and automation platforms
• Comfort learning and implementing new AI tools quickly and independently
• Experience with luxury travel coordination, including private aviation and high-end hospitality

PERSONAL QUALITIES

Skills can be learned. The following qualities cannot — and they are what will determine whether this role is a fit:

✔ Exceptionally organized and detail-oriented

✔ Proactive and resourceful — solves before being asked

✔ Calm, composed, and steady under pressure

✔ Polished, professional, and presentation-ready

✔ Warm, thoughtful, and emotionally intelligent

✔ Highly discreet and unconditionally dependable

✔ Execution-focused — closes every loop

✔ Technologically fluent and genuinely curious

✔ Naturally inclined to improve systems and reduce friction

✔ Comfortable balancing two principals, multiple priorities, and moving pieces simultaneously

WHAT SUCCESS LOOKS LIKE IN YEAR ONE

DAY 30

You understand both principals’ communication styles, priorities, and preferences — and are already anticipating needs rather than reacting to them.

DAY 60

You have taken full ownership of calendar management, travel coordination, and administrative systems. The principals feel the difference.

DAY 90

You have built or significantly improved at least three workflows using AI or automation tools, reducing manual work and increasing response speed.

DAY 365

You are indispensable. Both principals trust you completely — with their time, their information, their family, and their lives.

Pay: $150,000.00 - $200,000.00 per year

Benefits:

• Dental insurance
• Health insurance
• Paid time off
• Vision insurance

Work Location: In person