Virtual Executive Assistant to CEO (Full Time)

I am looking for a highly proactive, organized, and reliable Executive Virtual Assistant / Operations Coordinator to support me across multiple businesses and personal operating areas. This is not a basic admin role. I need someone who can think ahead, remove obstacles, organize chaos, follow up without being chased, and help keep important projects moving. I operate across several areas including HVAC sales and financing, real estate, Airbnb properties, Florida business expansion, vendor coordination, documents, inbox management, scheduling, research, and day-to-day executive support. The right person will act as a true assistant to the CEO, not just someone completing isolated tasks. Core Responsibilities: 1. Manage and organize emails, messages, documents, tasks, and follow-ups 2. Help manage calendars, meetings, reminders, deadlines, and priorities 3. Track open loops and make sure nothing important falls through the cracks 4. Coordinate with contractors, vendors, employees, property managers, cleaners, guests, and service providers 5. Assist with Airbnb property management, including guest communication, maintenance coordination, cleaner coordination, supply tracking, issue escalation, reviews, and basic listing support 6. Help organize real estate, business, financing, legal, operational, and administrative documents 7. Conduct research, compare options, summarize findings, and recommend clear next steps 8. Follow up with people on my behalf and keep momentum on active projects 9. Help manage task boards, CRM updates, spreadsheets, and operational trackers The Ideal Candidate: Extremely proactive and comfortable taking initiative Strong written and spoken English Very organized, detail-oriented, and reliable Comfortable working directly with a busy entrepreneur/CEO Able to handle many moving parts without getting overwhelmed Strong follow-up skills and accountability Able to communicate clearly, professionally, and directly Comfortable with real estate, Airbnb, operations, customer service, and business administration Good judgment, especially when dealing with guests, contractors, vendors, and sensitive information Able to summarize problems and bring solutions, not just forward issues Important Requirement: I do not want someone who waits for step-by-step instructions on every small task. I need someone who can say: “I noticed this issue and already followed up.” “Here are the three options and I recommend option two.” “This deadline is coming up, so I created a reminder and contacted the person responsible.” “This Airbnb guest issue needs attention, and here is how I suggest we handle it.” Experience Preferred: Executive assistant or operations assistant experience Airbnb / short-term rental management experience Real estate or property management experience Customer service experience Vendor and contractor coordination CRM, Google Workspace, spreadsheets, Notion, ClickUp, Trello, Asana, HubSpot, or similar tools Basic bookkeeping, invoice tracking, or document organization is a plus Location Preference: North American candidates are strongly preferred because of timezone alignment, communication style, and familiarity with North American business, real estate, and customer service standards. However, I am open to exceptional candidates in similar time zones who are highly reliable and fluent in English. Schedule: This can start part-time (25 weekly hours) and grow into a long-term role. I am looking for someone who can become a key support person over time. Availability during North American business hours is important. Some urgent Airbnb or business issues may require quick responses. What Success Looks Like: My inbox, calendar, tasks, and follow-ups are organized Airbnb guest issues are handled quickly and professionally Contractors and vendors are followed up with consistently Important business items do not get missed I spend less time chasing people and more time making decisions You become someone I can trust to manage details without constant supervision How to Apply: Please apply with: A short summary of your executive assistant or operations experience Any Airbnb, property management, or real estate experience you have The tools you are comfortable using Your availability and timezone An example of a time you proactively solved a problem before your client or manager had to ask Please start your application with the word PROACTIVE so I know you read the full posting. I am looking for someone long-term, sharp, organized, proactive, and trustworthy.