Conduit

The Calendar Group

Rising
thecalendargroup.com

The Calendar Group is a full-service staffing firm which provides professional and personalized staffing to high net worth families,

Open roles
104
New role every
~1.1 days
Posting trend
3.2× vs prior 90d

Company signals

Score: 77
Repost rate (90d) 0% GitHub org Yes First leadership hire Yes Posting cadence (90d/prior) 17.3x New cities (90d) 30 Buzzword-heavy listings 78% Growth-mode language 2% Role diversity (90d) 0 distinct titles

Job facts

Location
Remote · Tampa, Florida, United States of America
Workplace
Remote
Type
Full-time
Posted
Sep 02, 2026

Last verified live 1 month, 2 weeks ago · checked directly on the company's JazzHR / ApplyToJob

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Executive Assistant- 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.

Responsibilities:

  • 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.

Qualifications:

  • 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.