Simple Jobs in Ocoee, FL (NOW HIRING)

We are seeking an exceptionally organized, proactive, detail-oriented professional to oversee the daily operations of a busy entrepreneurial family household and multiple residential properties.

This is a high-trust leadership role for someone who naturally notices what others overlook, takes ownership without being asked, and thrives in creating order, efficiency, warmth, and excellence across many moving parts.

Our family owns and operates multiple businesses, employs household staff and contractors, manages several residential properties, and maintains a fast-paced but grounded family environment centered around our children.

We are not looking for a traditional assistant.

We are looking for someone who can serve as the operational hub of our family and household ecosystem — someone capable of managing people, overseeing projects, coordinating staff and vendors, maintaining high standards across properties, and proactively solving problems before they reach us.

The ideal candidate is highly capable, discreet, service-minded, organized, observant, and comfortable leading others with both warmth and accountability.

Core Responsibilities

Household & Property Operations

• Oversee the daily operations and presentation of multiple homes and properties
• Conduct routine walkthroughs and inspections to ensure properties remain highly functional, organized, clean, and guest-ready
• Identify maintenance, cleaning, safety, and organizational issues proactively
• Coordinate contractors, vendors, repair professionals, landscapers, cleaners, and maintenance personnel
• Ensure work is completed thoroughly, correctly, and on time
• Maintain and manage recurring maintenance schedules and property task lists
• Oversee renovation projects and coordinate timelines, priorities, and follow-through

Staff Leadership & Coordination

• Coordinate schedules and responsibilities for household staff, nannies, cleaners, assistants, and vendors
• Create accountability systems and maintain operational standards
• Follow up consistently to ensure tasks are completed properly without requiring owner involvement
• Assist with interviewing, onboarding, training, and evaluating household and support staff
• Help cultivate a respectful, family-oriented, high-performance culture

Family & Lifestyle Management

• Oversee household inventories, supplies, and organization systems
• Coordinate, birthdays, holidays, and employee appreciation efforts
• Ensure homes feel welcoming, thoughtful, prepared, and comfortable for family and guests
• Assist in reducing operational burdens and daily decision fatigue for principals

Executive Support & Operational Oversight

• Serve as a liaison between principals and household/business staff
• Help organize priorities, action items, and operational communication
• Attend meetings when needed and help track follow-through and execution
• Create systems, processes, checklists, and organizational improvements
• Anticipate needs and proactively resolve issues

The Ideal Candidate

• Naturally observant and detail-oriented
• Strong leadership and follow-through skills
• Able to hold people accountable professionally and respectfully
• Excellent judgment and problem-solving ability
• Highly organized with strong executive functioning skills
• Calm under pressure and capable of managing many moving parts simultaneously
• Trustworthy, discreet, and highly dependable
• Comfortable around children, families, household staff, contractors, and executives alike
• Service-minded without needing constant direction
• Able to notice what needs attention without being instructed on every detail

Experience Preferred

• Estate management, luxury hospitality, executive support, operations management, household management, property management, or family office experience strongly preferred
• Experience managing staff and vendors preferred
• Project management experience is highly valued
• Backgrounds in hospitality, operations, executive assistance, or private service environments are a plus

This is intended to be a long-term, high-trust role with significant opportunity for autonomy, and impact.

To Apply

Please submit:

• Resume
• Brief cover letter describing why you believe you would excel in this type of role
• Cover letter should include examples of situations where you proactively identified and solved problems without direction.

We look forward to welcoming the perfect person into our family.