Personal Assistant / Executive Support

About this role

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.

Essential Duties and Responsibilities 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.

Required Knowledge, Skills, and Abilities • 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. • Familiarity with large residential or rural property operations. • Strong business acumen and the ability to prioritize effectively.

Physical Demands   The physical demands described are representative of those that must be met by any employee to successfully perform the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions. While performing the duties of this job, the employee frequently communicates with employees and clients and must be able to exchange accurate information. Additional functions include standing and/or sitting in a stationary position for extended periods of time; using a computer/laptop in an office environment with natural and/or fluorescent lighting (50%+); navigating between office building floors; regularly attending off-site meetings or events; and lifting up to 35 lbs. unassisted. The employee is regularly required to use a computer/laptop/iPad in an office environment with natural and/or fluorescent lighting and to navigate between office building floors.

Work Environment  

The work environment characteristics described here are representative of those employees may   encounter   while performing the essential functions of this job. Most often   works   in   a home environment , and   travel   is   required .    Employee frequently works   alone and with others. Frequently exposed to variable work environments, including unique conditions outside a typical office environment. May be exposed to environmental conditions and variable weather, including rain, snow, wind, cold, and heat.    Ability and willingness to work near animals (dogs and cats).

Additional Job Description:

  We offer our full-time employees a comprehensive benefits package that include

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