Executive Assistant- Tampa, Florida in Tampa, Florida at The Calendar Group

A rapidly growing entrepreneurial family in Tampa, FL is seeking a highly experienced, tech-savvy, and proactive Executive Assistant to support the CEO and VP of Operations across multiple businesses. This is a fast-paced role for someone who can manage constantly changing priorities, anticipate needs, and keep up with an entrepreneurial environment where no two days are the same.

• Provide high-level administrative support to the CEO and VP of Operations.
• Manage calendars, scheduling, meetings, and communications.
• Coordinate domestic and international business travel and itineraries.
• Handle last-minute travel changes, cancellations, and rescheduling.
• Manage follow-ups, projects, and administrative priorities across multiple businesses.
• Assist with meetings, presentations, and business coordination.
• Use Microsoft 365, Excel, and other technology platforms to support daily operations.
• Serve as a trusted gatekeeper and point of contact when appropriate.
• Anticipate needs and proactively address issues that arise.
• Adapt quickly as business priorities change.
• Provide occasional travel support as the principals' businesses continue to expand.

• Significant experience supporting a CEO, founder, entrepreneur, or other senior executive.
• Highly organized, proactive, and exceptionally responsive.
• Strong technology skills, including proficiency with Microsoft 365 and Excel.
• Comfortable using AI and cloud-based tools.
• Excellent written and verbal communication skills.
• Able to manage multiple priorities in a fast-paced environment.
• Strong judgment, discretion, and attention to detail.
• Resourceful and capable of working independently.
• Comfortable working in an entrepreneurial environment.
• Willingness to travel occasionally.

Salary: $80,000–$120,000 annually

Schedule: Full-time position. The role will primarily be remote/hybrid, with the ability to attend meetings in person as needed. The EA should be comfortable with communication outside traditional business hours and must be flexible to accommodate the fast-moving nature of the principals' businesses.