Executive Administrative Assistant to CEO

Role Overview

This is a high-responsibility, full-time on-site opportunity based in Downtown Miami, FL, open only to local candidates. The position supports a CEO who leads several businesses across different industries and requires a dependable, highly proactive partner to help manage both business and personal priorities. The role also extends support to his wife and involves working across a large organization with more than 90 employees.

The right person will act as a true right-hand operator, helping reduce the CEO’s workload by managing complex coordination, execution, follow-through, and day-to-day logistics. The work is fast-moving, highly varied, and suited to someone who enjoys ownership, problem-solving, and operating in an environment where priorities can shift quickly.

Schedule

Monday through Friday, 9:00 AM to 5:00 PM. This is a full-time on-site position.

Executive and Business Support

• Oversee demanding calendars, appointments, and business logistics so schedules stay organized and productive.
• Sort and prioritize inboxes, manage sensitive correspondence, and ensure key messages are handled carefully.
• Support the sales pipeline and contract execution using HubSpot, PandaDoc, and DocuSign.
• Act as a filter for internal requests, make sure important items reach the CEO for review, and coordinate meetings across teams with strong follow-up.
• Drive special projects from planning through completion, keeping multiple business entities aligned and moving forward.

Travel and Logistics

• Arrange complex luxury travel plans, including international itineraries that may span multiple time zones.
• Use loyalty programs, concierge services, and detailed agendas to improve efficiency and comfort during travel.
• Coordinate longer personal trips, retreats, and unique experiences while preparing backup plans for disruptions.
• Create and maintain travel briefings, logistics trackers, and documents for international travel requirements.

Personal and Household Operations

• Coordinate household activity with the house manager, vendors, cleaners, and other service providers.
• Track maintenance schedules and help keep the home operation running smoothly.
• Handle personal financial transactions and manage vendor relationships.
• Organize wellness visits, dining plans, social events, entertainment, groceries, and other household or lifestyle needs.
• Work closely with the CEO’s partner to make sure personal priorities are handled seamlessly.

Systems, Documentation, and Continuous Improvement

• Improve visibility and workflow through tools such as ClickUp, Slack, and AI-based solutions.
• Build and maintain trackers, SOPs, and repeatable process documentation.
• Adapt to changing needs over time, as the role will continue to evolve.
• The core objective is to give the CEO back more of his time through strong execution and ownership.

Requirements

• At least 3 years of experience in a blended Executive Assistant, Personal Assistant, or Life Manager capacity, ideally within a fast-growing startup or entrepreneurial setting.
• Strong technical comfort and frequent use of AI tools, especially Claude, along with advanced skills in GSuite, Slack, CRM platforms, ClickUp, Notion, and spreadsheets.
• Advanced ability to coordinate international travel and manage high-level logistics.
• Must be based in Miami, hold a valid driver’s license, and own a car.
• Applicants should be highly proactive, solutions-focused, able to handle blunt feedback, and comfortable with rapid context switching.
• The role calls for a highly driven, competitive mindset and strong resilience in a demanding environment.

Compensation and Benefits

The annual salary range is $70,000 to $90,000, with performance-based increases available.

Benefits include Anthem Blue Cross Platinum PPO health insurance with a $0 deductible, 36 PTO days per year, direct mentorship, a pathway toward a Chief of Staff role, and access to high-level leaders and distinctive travel experiences.

Confidentiality and Work Style

This position requires absolute discretion and strict confidentiality. Successful candidates will be comfortable working with complexity, shifting demands, and a high-ownership environment that can sometimes feel chaotic.