Personal Assistant ​/ Executive Support

Job Description

We are seeking a highly organized, discreet, and proactive Personal Assistant to support an executive’s schedule and 500-acre household property. This role will monitor the executive’s appointments and movements, manage daily administrative tasks, oversee domestic services, assist with travel, and handle email correspondence. The ideal candidate will serve as a trusted extension of the CEO, bringing sound judgment, discretion, organizational excellence, and business acumen.

This individual will anticipate needs, solve problems proactively, balance competing priorities, and help keep the CEO focused on the highest-value opportunities. Success requires professionalism, adaptability, confidentiality, integrity, and the ability to build strong relationships at all levels.

• Executive Support & Calendar Management Manage and optimize the CEO’s complex business and personal calendar, ensuring priorities align with organizational and personal objectives. Monitor daily schedules, appointments, meetings, and commitments while proactively identifying conflicts and recommending adjustments. Coordinate executive travel arrangements, including flights, lodging, transportation, itineraries, and related logistics. Prepare schedules, briefing materials, and supporting information to ensure the CEO is well-prepared for meetings, events, and engagements.
  
  Track key follow-up items, commitments, and deadlines to ensure timely execution.
• Communication Management Manage and prioritize email correspondence, drafting responses and ensuring important matters receive appropriate attention. Serve as a liaison between the CEO and internal or external stakeholders, maintaining professionalism and confidentiality at all times. Screen incoming requests and communications, exercising sound judgment regarding urgency and appropriate escalation.
• Household & Property Management Coordinate and manage relationships with household staff, contractors, service providers, and vendors. Schedule and oversee maintenance projects, repairs, inspections, and seasonal property activities. Manage household-related budgets, invoices, service agreements, and vendor payments. Monitor inventory and procurement of household, property, and event-related supplies.
• Personal & Family Support Coordinate personal appointments, reservations, transportation, errands, and special requests. Assist with family travel planning, scheduling, and logistics. Support personal events, gatherings, and hospitality needs as requested. Handle sensitive personal matters with the highest degree of professionalism and discretion.
• Project & Operations Coordination Manage special projects on behalf of the CEO and family, ensuring deadlines, budgets, and objectives are achieved. Anticipate needs, identify potential issues, and proactively develop solutions before problems arise.
• Confidentiality & Trust Maintain strict confidentiality regarding all business, financial, family, and personal matters. Handle sensitive information with sound judgment, discretion, and professionalism. Serve as a trusted extension of the CEO, consistently demonstrating integrity, loyalty, and reliability.

• Experience supporting a CEO, business owner, executive leader, high-net-worth individual, or family office.
• Proven experience managing complex schedules, travel arrangements, meetings, and executive communications.
• Experience coordinating multiple priorities in a fast-paced environment while maintaining exceptional attention to detail.
• Demonstrated ability to handle highly confidential business and personal information with discretion and professionalism.
• Valid driver’s license with a clean driving record and ability to travel locally as needed.
• Proficiency in Microsoft 365 applications including Outlook, Teams, Word, Excel, and PowerPoint.
• Strong written and verbal communication skills.
• Ability to work independently, exercise sound judgment, and adapt quickly.
• Preferred:
  Experience supporting a principal in both professional and personal/household contexts.
• Preferred:
  Familiarity with large residential or rural…