Executive Assistant To The Owner Jobs (NOW HIRING)

Executive Assistant to the Owner

Position Summary

The Owner is responsible for the leadership, strategic direction, and oversight of multiple successful businesses operating across a variety of industries. Due to the scope and demands of these responsibilities, we are seeking a highly organized, proactive, discreet, adaptable, and exceptionally capable Executive Assistant to the Owner to provide comprehensive executive, administrative, personal, and lifestyle support.

The Executive Assistant will serve as a trusted point of coordination for the Owner, managing professional and personal scheduling, correspondence, travel, appointments, personal commitments, errands, events, wardrobe coordination, and other responsibilities necessary to support the Owner’s professional and personal priorities.

This is a full-time, in-person position located in or near Palm Harbor, Florida and requires an individual who can work effectively in a dynamic, fast-paced environment with frequently changing priorities. Occasional travel may be required to support the Owner’s professional and personal commitments.

The ideal candidate will possess exceptional organizational skills, sound judgment, discretion, initiative, professionalism, and the ability to manage multiple priorities with minimal supervision. This individual must be comfortable anticipating needs, solving problems independently, coordinating multiple people and resources, and ensuring that responsibilities are followed through to completion.

The Executive Assistant will work closely with the Owner and a wide range of employees, executives, business associates, vendors, service providers, and other professional and personal contacts to ensure that responsibilities are coordinated efficiently and executed to a consistently high standard.

Key Responsibilities

Executive & Administrative Support

• Manage and maintain the Owner’s professional and personal calendar, including meetings, appointments, commitments, and events.
• Coordinate schedules across multiple businesses, individuals, and competing priorities.
• Manage correspondence, communications, follow-ups, and administrative matters on behalf of the Owner.
• Prepare, organize, and maintain documents, schedules, itineraries, presentations, and other materials as needed.
• Track deadlines, commitments, outstanding items, and follow-up activities to ensure timely completion.
• Assist the Owner with prioritizing responsibilities and managing time effectively.
• Monitor upcoming obligations and proactively identify items requiring preparation, coordination, or follow-up.
• Coordinate with employees, executives, clients, vendors, business partners, and other professional contacts on behalf of the Owner.
• Maintain accurate and organized records of professional and personal commitments.

Personal & Lifestyle Support

• Manage personal appointments, reservations, commitments, and private scheduling.
• Coordinate personal errands, purchases, returns, deliveries, and other time-sensitive tasks.
• Research and arrange personal services, appointments, reservations, experiences, and activities as requested.
• Coordinate household and lifestyle-related responsibilities as needed.
• Assist with wardrobe organization and coordination, including shopping, alterations, dry cleaning, packing, and event-specific attire.
• Coordinate personal events, dinners, celebrations, social engagements, and other activities.
• Communicate with personal service providers, vendors, venues, and other contacts on the Owner’s behalf.
• Maintain an exceptionally high level of discretion and confidentiality regarding all personal matters.

Travel & Event Coordination

• Coordinate domestic and international travel arrangements, including flights, accommodations, transportation, reservations, and itineraries.
• Prepare detailed travel itineraries and ensure all necessary arrangements are confirmed in advance.
• Coordinate travel-related logistics, including transportation, packing, wardrobe, reservations, and scheduling.
• Research destinations, restaurants, venues, activities, and other experiences as requested.
• Coordinate business and personal events from initial planning through completion.
• Communicate with venues, vendors, event staff, and other parties to ensure arrangements are executed efficiently and professionally.
• Resolve unexpected travel, scheduling, or event-related issues promptly and professionally.

Communication & Relationship Management

• Serve as a professional liaison between the Owner and employees, vendors, business associates, service providers, and other contacts.
• Coordinate multiple individuals and moving parts to ensure plans and commitments are executed effectively.
• Establish and maintain professional relationships with vendors and service providers.
• Follow up consistently to ensure tasks, requests, and commitments are completed.
• Represent the Owner with professionalism, discretion, sound judgment, and appropriate communication.
• Determine when matters can be independently handled and when they require escalation to the Owner.
• Maintain a high level of professionalism when interacting with individuals on behalf of the Owner.

Organization & Proactive Support

• Anticipate the Owner’s needs and proactively address responsibilities before they become issues.
• Maintain organized systems for managing schedules, commitments, contacts, travel, events, and personal responsibilities.
• Identify potential scheduling conflicts, logistical concerns, or other issues and recommend practical solutions.
• Assist with coordinating multiple priorities simultaneously while maintaining accuracy and attention to detail.
• Take ownership of assigned responsibilities and ensure tasks are followed through to completion.
• Support special projects and other responsibilities as assigned by the Owner.
• Continuously identify opportunities to improve organization, efficiency, communication, and overall support.

Required Qualifications

• High school diploma or equivalent required; Associate’s or Bachelor’s degree in Business Administration, Communications, Hospitality, Management, or a related field preferred.
• Previous experience as an Executive Assistant, Personal Assistant, Administrative Assistant, Office Manager, or similar support role required.
• Experience supporting an executive, business owner, entrepreneur, or senior leader preferred.
• Demonstrated ability to manage complex schedules, competing priorities, and time-sensitive responsibilities.
• Exceptional organizational and time-management skills.
• Excellent written, verbal, and interpersonal communication skills.
• Strong problem-solving, decision-making, and critical-thinking skills.
• Demonstrated ability to work independently and exercise sound judgment.
• High level of attention to detail, accuracy, accountability, and follow-through.
• Ability to handle sensitive and confidential business and personal information with complete discretion.
• Ability to manage frequent changes in priorities and respond effectively to unexpected situations.
• Proficiency with Microsoft Office, Google Workspace, calendar management systems, and other organizational technologies.
• Must be available to work full-time.
• Must reside in or be able to reliably commute to the Palm Harbor, Florida area.
• Must be willing and able to travel occasionally as required.
• Must have reliable transportation for local business and personal errands, appointments, and other responsibilities.

Preferred Qualifications

• Bachelor’s degree in Business Administration, Communications, Hospitality, Management, or a related field.
• Previous experience supporting a high-level executive, entrepreneur, business owner, or individual with a complex professional and personal schedule.
• Experience managing both executive and personal assistant responsibilities.
• Experience coordinating domestic and international travel.
• Experience coordinating events, social engagements, or private functions.
• Experience with wardrobe, lifestyle, household, or concierge-related coordination.
• Experience working in a fast-paced, high-expectation environment.
• Demonstrated ability to anticipate needs and operate proactively with minimal direction.
• Experience coordinating multiple vendors, service providers, or other third parties.

Key Skills & Competencies

Executive & Personal Support

Calendar & Schedule Management

Travel & Event Coordination

Organization & Time Management

Communication & Correspondence

Confidentiality & Discretion

Problem Solving & Decision-Making

Proactive Planning & Anticipation

Vendor & Relationship Management

Personal & Lifestyle Coordination

Project & Task Management

Attention to Detail & Accuracy

Adaptability & Flexibility

Professionalism & Sound Judgment

Multitasking & Prioritization

Follow-Through & Accountability

Communication Resilience & Professional Maturity

Work Environment & Expectations

The Executive Assistant is expected to maintain a high level of professionalism, discretion, accountability, responsiveness, and confidentiality while supporting the Owner’s professional and personal responsibilities.

This is a full-time, in-person position located in or near Palm Harbor, Florida. The role requires flexibility and the ability to adapt to changing schedules, priorities, and circumstances. Occasional domestic travel may be required in support of the Owner’s professional or personal commitments.

The Owner communicates in a direct, candid, and straightforward manner. The successful candidate must be comfortable receiving direct feedback, communicating openly, and maintaining professionalism in a fast-paced, high-expectation environment. The ability to remain composed, adaptable, and solution-oriented when circumstances change is essential.

The successful candidate must be able to roll with the punches, manage unexpected requests or changes in direction, and adjust priorities without becoming easily discouraged. This position requires emotional maturity, confidence, discretion, sound judgment, and the ability to receive constructive feedback without taking direct communication personally.

The Executive Assistant is expected to take ownership of responsibilities, anticipate needs, identify potential issues, and proactively develop solutions rather than relying solely on direction from the Owner.

Due to the highly confidential and personal nature of this position, the Executive Assistant must demonstrate exceptional integrity, discretion, judgment, and respect for privacy at all times.

The successful candidate will become a trusted extension of the Owner and will be expected to maintain a high standard of professionalism in all interactions with employees, business associates, vendors, service providers, and personal contacts.