Heart Me & Follow is looking for a highly organized, proactive, and resourceful Executive & Personal Assistant to work directly with the Founder & CEO in Naples, Florida.

This is not a traditional administrative role. The purpose of this position is to protect the CEO’s time, reduce administrative workload, anticipate needs, and ensure important tasks, communications, meetings, travel, and follow-ups are handled efficiently.

The ideal candidate takes ownership, learns quickly, communicates exceptionally well, and enjoys creating order in a fast-moving entrepreneurial environment.

KEY RESPONSIBILITIES

• Own and manage the CEO’s calendar, meetings, appointments, and scheduling priorities

• Help manage and organize the CEO’s inbox and identify communications that truly require his attention

• Track commitments, deadlines, and follow-ups with team members, partners, vendors, and external contacts

• Coordinate business and personal travel from beginning to end, including flights, hotels, transportation, reservations, and itineraries

• Prepare concise context and relevant information before important meetings

• Capture action items and ensure follow-ups are completed

• Conduct research and present clear recommendations or 2–3 strong options rather than simply presenting problems

• Coordinate personal appointments, reservations, purchases, services, and administrative needs when necessary

• Act as a communication bridge between the CEO and the Heart Me & Follow team when appropriate

• Anticipate potential issues and solve them before they require the CEO’s attention

• Handle confidential business and personal information with exceptional discretion

WHAT WE’RE LOOKING FOR

• Extremely organized and detail-oriented

• Proactive, resourceful, and solution-oriented

• Strong sense of ownership and follow-through

• Excellent written and verbal communication

• Comfortable working in a fast-paced entrepreneurial environment

• Able to prioritize independently and manage multiple responsibilities

• Tech-savvy and comfortable learning new tools quickly

• Professional, reliable, discreet, and trustworthy

• Fluent English required; Spanish strongly preferred

• Experience as an Executive Assistant, Personal Assistant, Administrative Assistant, Operations Coordinator, or similar role is preferred

Experience matters, but judgment, organization, initiative, and the ability to learn quickly matter even more.

LOCATION

Naples, Florida — primarily in-person.

This is a full-time position working closely with the Founder & CEO. Reliable transportation is required.

COMPENSATION

$22–$28/hour, depending on experience and capabilities.

Performance and compensation review after the initial 90-day period, with meaningful long-term growth potential for someone who becomes a highly effective and trusted extension of the CEO.

WHAT SUCCESS LOOKS LIKE

A great Executive Assistant doesn’t wait for every instruction. They anticipate what’s coming, handle what they can independently, and bring the CEO only the decisions that truly require his attention.

The goal is simple: protect the CEO’s time so he can remain focused on strategy, growth, relationships, and high-value decisions.

HEART ME & FOLLOW jobs

Executive & Personal Assistant to Founder/CEO

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