Executive Operations Assistant | Real Estate & Transaction Support

Do you love keeping moving pieces organized, catching details others miss, and solving problems before they reach the CEO? We are hiring a business-minded Executive Operations Assistant to support leadership across administration, operations, financial organization, and real estate. This is not a basic VA or data-entry position. This role is ideal for someone with an analytical or technical mind who is comfortable with responsibility, numbers, systems, deadlines, and rapidly changing priorities. If you naturally think, “What needs to happen next?” and take ownership without waiting to be told every step, this may be the right opportunity for you. COMPENSATION & SCHEDULE * $800/month guaranteed base compensation * Opportunity to earn an additional $25 each week by meeting the documented weekly performance standard * Opportunity to earn up to $900 total in a standard four-bonus-week month * Monday–Friday: 10:00 AM–7:00 PM Eastern Time * Weekday breaks: 45 minutes total — one 30-minute break and one 15-minute break * Every other Saturday: 11:00 AM–5:00 PM Eastern Time Weekly performance bonuses are earned separately from base compensation and are based on documented standards for: * Attendance and punctuality * Accuracy * Meeting deadlines * Communication * Follow-up * Ownership and initiative CORE AREAS OF RESPONSIBILITY *Executive & Administrative Support * Keep the CEO organized by managing priorities, deadlines, calendars, reminders, research, follow-ups, and special projects * Track assignments across multiple business priorities and proactively flag delays, missing information, and risks * Follow up with team members and outside parties without requiring the CEO to chase routine items BUSINESS OPERATIONS & REPORTING * Build and maintain accurate Google Sheets, trackers, reports, business records, and operational documentation * Work with numbers and financial information accurately and carefully * Research operational issues, organize information, identify the next action, and bring possible solutions—not just problems FINANCIAL ORGANIZATION * Manage the bill calendar, including due dates, recurring expenses, payment schedules, amounts, alerts, and verification of financial information * Maintain accurate financial spreadsheets and organized payment records REAL ESTATE & TRANSACTION COORDINATION * Assist with real estate operations and transaction coordination, including contract-to-close tracking, CRM records, documentation, signatures, deadlines, and communication with transaction parties * Keep important transaction requirements organized, visible, and moving forward CANDIDATE PROFILE REQUIRED * Bachelor's degree required * Professional business experience required * Exceptionally clear, fluent English for U.S. business calls and strong professional writing * Strong numerical skills and proficiency in Google Sheets and/or Excel * Excellent judgment, organization, multitasking, prioritization, follow-through, and attention to detail * Tech-savvy, resourceful, accountable, and comfortable making decisions independently * Comfortable working directly with a high-expectation, fast-moving CEO Analytical, business, technical, finance, accounting, real estate, computer science, data, or operations backgrounds are especially relevant. Real estate or transaction coordination experience is a strong advantage. WHAT SUCCESS LOOKS LIKE You will be successful in this role if: * Leadership does not need to repeatedly remind you about assigned responsibilities * Important deadlines, transactions, bills, and follow-ups stay organized and visible * Your work is accurate, and you double-check important numbers and details * You communicate blockers early rather than allowing problems to grow * You take ownership of resolving problems you can reasonably handle * You anticipate what needs to happen next * Over time, you reduce the CEO's administrative workload and become a trusted extension of leadership THIS ROLE IS NOT FOR YOU IF... Please do not apply if: * You need constant supervision or repeated reminders * You regularly miss deadlines or arrive late * You frequently lose track of details * You struggle with numbers, spreadsheets, or multiple priorities * You have difficulty adapting to rapid changes * You wait for exact step-by-step instructions instead of using judgment * You hide mistakes or avoid communicating problems * You are looking only for a short-term position HOW TO APPLY Please answer every question below in your Upwork proposal: 1. Tell us about your degree and the most relevant business or operations experience you have. 2. What is the most complex responsibility you have owned for an executive or business? 3. If you have real estate experience, explain your role and any transaction coordination responsibilities. 4. Describe a spreadsheet, tracker, report, or financial process you built or maintained. 5. You receive five urgent requests at once. How do you decide what happens first? 6. Give an example of a process you improved or a problem you solved without being told exactly how. 7. How do you personally prevent missed deadlines and forgotten follow-ups? 8. List the business, CRM, real estate, project-management, spreadsheet, and AI tools you know well. 9. Confirm that the required Eastern Time schedule works consistently for you. 10. Start your proposal with “OPERATIONS FIRST”. LONG-TERM OPPORTUNITY We want a long-term team member who can grow into a high-trust role. Strong performance in this position means becoming more valuable over time by: * Understanding the businesses * Anticipating needs * Maintaining accurate systems * Bringing useful insight * Taking ownership without needing to be chased If you are highly organized, analytical, proactive, dependable, and motivated to become an essential part of a growing business, we want to hear from you.