Operating Executive Jobs in Orlando, FL (NOW HIRING)

We are looking for an exceptional Executive Assistant / Chief of Staff to serve as a trusted right hand to a senior executive. This is not a traditional administrative role. We are looking for someone who is highly organized, exceptionally resourceful, comfortable operating in a fast-moving environment, and motivated by the challenge of making things happen.

The ideal candidate has significant experience managing highly complex executive calendars—potentially across four or five calendars simultaneously—and can confidently navigate competing priorities, last-minute changes, shifting demands, and sensitive information.

There will be relatively little flight or travel coordination compared with a traditional Executive Assistant role. Instead, the heart of this position is calendar mastery, prioritization, problem-solving, follow-through, and being the person who figures out how to get things done.

This role is ideal for someone who wants to grow beyond the traditional Executive Assistant position. The right person will have the opportunity to take on increasing levels of responsibility and could ultimately evolve into a Chief of Staff or broader strategic operational role.

What You'll Do

Executive & Calendar Management

• Own and proactively manage the executive's highly complex calendar, including coordinating across 4–5 calendars and multiple stakeholders.
• Serve as the gatekeeper and strategic owner of the executive's time.
• Constantly evaluate priorities and make thoughtful decisions about what deserves the executive's time and attention.
• Resolve scheduling conflicts quickly and creatively, often with incomplete information or significant time constraints.
• Anticipate conflicts and bottlenecks before they become problems.
• Coordinate meetings involving internal teams, clients, partners, family members, and other stakeholders.
• Ensure the executive is fully prepared for meetings, commitments, and important conversations.
• Protect focus time while remaining responsive to urgent and changing priorities.
• Manage last-minute changes with calmness and professionalism.

Problem-Solving & Execution

• Take ownership of problems rather than simply identifying them.
• Be the person who hears, "We need to figure this out," and immediately starts figuring it out.
• Navigate obstacles, competing priorities, difficult logistics, and unexpected situations with ease.
• Develop solutions independently and use sound judgment about when to act and when to escalate.
• Follow through relentlessly—if something is assigned to you, make sure it gets done.
• Build relationships and leverage resources to accomplish things that may initially seem difficult or impossible.
• Bring a "whatever it takes to get it done" mindset while exercising good judgment, discretion, and professionalism.

Executive Support & Operations

• Serve as a trusted extension of the executive.
• Keep track of commitments, follow-ups, deadlines, and outstanding items.
• Help create structure around the executive's professional and, at times, personal responsibilities.
• Coordinate with colleagues, vendors, service providers, and other outside parties as needed.
• Handle confidential and sensitive information with absolute discretion.
• Identify opportunities to improve how the executive operates and proactively implement better systems and processes.
• Take on projects and responsibilities outside the traditional EA scope as trust and familiarity with the business grow.

Family & Personal Support

From time to time, the role will include supporting the executive's family and personal responsibilities. This may include:

• Occasional pickup or drop-off of children.
• Coordinating appointments, activities, or other family logistics.
• Helping solve personal or household-related logistical challenges.
• Stepping in when needed to ensure important commitments are handled smoothly.

These responsibilities will be occasional but are an important part of being a truly trusted partner to the executive.

Who You Are

You are someone who makes things happen.

You don't get stuck when the obvious solution doesn't work. You find another way. You are comfortable with ambiguity, shifting priorities, and situations where there isn't a clear playbook.

You are likely to describe yourself as:

• Exceptionally organized and detail-oriented without being rigid.
• Calm under pressure.
• Highly resourceful and solutions-oriented.
• Proactive rather than reactive.
• Discreet and trustworthy.
• Extremely dependable.
• Comfortable making decisions independently.
• A strong communicator who knows how to work with people at all levels.
• Someone who takes ownership and doesn't need to be chased.
• Someone who enjoys being the person others can rely on.

Most importantly, you have a genuine "whatever it takes—just make sure it gets done" mentality.

What We're Looking For

• 5+ years of experience supporting a senior executive, entrepreneur, founder, or similarly demanding leader.
• Demonstrated experience managing complex, multi-calendar environments, ideally involving four or more calendars.
• Exceptional organizational and time-management skills.
• Strong judgment and the ability to prioritize competing demands.
• Proven ability to manage frequent changes and last-minute requests without becoming overwhelmed.
• Excellent written and verbal communication skills.
• High level of technological proficiency and comfort learning new tools quickly.
• Ability to maintain strict confidentiality.
• A valid driver's license and reliable transportation, given the occasional need to assist with family logistics.
• Willingness and flexibility to occasionally handle personal or family-related responsibilities.
• A track record of taking on increasing responsibility and operating beyond a narrowly defined job description.