Executive Assistant

The Executive Assistant reports directly to the CEO and is responsible for saving time & money, keeping the CEO organized, and ensuring alignment and focus on high-priority tasks. This role encompasses business support, personal assistance, and management of both short-term and long-term rental operations. The ideal candidate, highly organized, process-driven, and capable of thinking independently to handle a dynamic workload while bringing structure and standardization to the CEO’s busy schedule.

Primary Duties
Business Functions
· Manage CEO’s calendar – Own and protect the CEO’s calendar, proactively schedule and prioritize meetings (internal/external)., buffer time for deep work, travel and breaks, prep and align the day/week/month in advance – no surprises.
· Collect and organize tasks – From email, chat platforms, and other sources to maintain a clear and prioritized daily task list and morning check-ins to reviews and communicate daily priorities and tasks.
· Manage CEO meetings – Formulate agendas, notes, background, key questions before meetings; take notes during meetings, highlight action items, Follow-up with team members to ensure takes are completed.
· Travel planning and Logistics – Book and manage all aspects of travel: flights, hotel, cars, itineraries, anticipate and prevent problems (cancellations, delays, preferences)
· Record and manage timesheets – In PSA software (ConnectWise) for self and CEO, ensuring accurate submission by the end of each day.
· Social Media Management – Draft and edit content and responses for social media platforms, including light video editing tasks, using AI to discover and generate content & trends and responding to inquiries.
· Triage, draft, and manage emails - only elevate what truly requires executive attention, act as a gatekeeper and filter out noise, handle routine correspondence and communications.
· Information and Document Management – Maintain organized, easily accessible records, reports, and documents; draft, proofread, and manage critical documents; manage confidential and sensitive information with discretion.
· Project and Initiative Support – Manage special projects (internal/external) from start to finish; research, gather data, analyze, and present options to help executive decision-making; coordinate cross-departmental initiatives with clients, partners, vendors, and internal teams.
· HR and Staff Coordination – Help recruit, interview, and onboard staff. Coordinate and ensure accurate documentation (emergency contacts, HR paperwork). Follow up on internal deadlines, timesheets, and staff accountability.
· M&A Research & Sales Administration – Proactively collect and maintain data on potential MSP acquisition targets. Coordinate outreach and follow up communications with targets companies. Assist with CRM hygiene, BDR workflows, and sales pipeline tasks related to acquisitions or growth initiatives.
· Track Cost Savings – Maintain a master spreadsheet of all purchases for home, beach and business. Identify cost-saving opportunities and track overspend from incorrect or wasteful orders. Earn incentives based on measurable savings and reduced waste.
· Document Recurring Tasks & Functions – Maintain and continuously update the executive assistant guide with recurring tasks and procedures. Standardize workflows for repeatable functions to ensure consistency and easy delegation. Prepare documentation for eventual migration into Hudu or another internal knowledge system.

Short-Term Rental Management
· Maximize Occupancy and Profit – Track vacancy rate weekly, adjust pricing and availability to boost revenue and occupancy rates per night. Split or combine stays strategically to minimize vacancies.
· Coordinate with Vendors - Manage cleaners, linen services, and maintenance vendors. Ensure supplies are stocked and delivered to the right place, on time. Resolve issues fast – no delays, no drama.
· Own Guest Communication. - Be the one-stop shop for all guest contact – before, during, and after their stay. Handle check-ins, questions, and problems without involving hosts. Keep response times tight to protect ratings and reduce headaches.
· Manage the Calendar and Listing – Keep listings updated and accurate. Sync calendars to avoid double bookings. Block dates for maintenance or personal use as needed.
· Maintain Quality Standards – Confirm cleanings are completed properly after each stay. Ensure the property is guest-ready-fully stocked, fully functional. Proactively identify and address anything that could take a review.

Personal Assistance

· Order Household Essentials – Purchase supplies, clothing and other necessities as they run low. Price shop smartly and ensure on-time delivery to the right location.
· Schedule Appointments and Events – Book and manage all family-related appointments- doctor, dentist, school events, etc. Send reminders and coordinate schedules to avoid conflicts.
· Coordinate Family Travel – Align travel plans with everyone’s calendar – no overlaps, no surprises. Handle bookings, confirmations, and changes across multiple itineraries.
· Book & Manage Family Trips – Take care of all travel arrangement: flights, hotels, transportation, dining. Communicate plans clearly with all parties involved ahead of time.
· Maintain the Household Calendar – Keep a shared calendar of family activities, appointments, and commitments. Proactively update it as plans shift and notify relevant people of changes

Qualifications

Education & Experience
· Proven experience as a Executive Assistant, Personal Assistant, or in a similar role for a minimum of two full years in the same role.
· Familiarity with managing multiple priorities and working in a fast-paced environment.
· History of calling and speaking directly to new and unknown people
Skills & Proficiencies
· Excellent English communication skills, both written and spoken with a demonstrated history of critical thinking and direct, honest communication
· Highly organized and process-driven, with a strong attention to detail.
· Familiarity with task management software and productivity tools.
· Proficiency in professional communications platforms (e.g., Teams, Slack).
· Strong decision-making skills and the ability to prioritize effectively in a dynamic environment.
· Comfortable learning new tools and technologies and standardizing processes.
· Calm, collected, and methodical in managing workload.
· Unafraid to pick up the phone and call people.

Work Environment
· The role requires working from an office from 7am to 4pm EST Monday to Friday.
· Occasional weekend availability is required for rental-related tasks and urgent requests.
· Remote support may be needed when the CEO is traveling during off hours.

Compensation and Benefits
· Competitive monthly salary.
· Paid leave and performance bonuses are based on meeting KPI’s.
· HMO benefits
· Equipment and internet and mobile phone reimbursement.
· Opportunities for professional development and access to training resources.
· Travel reimbursement and per diem for approved events.