EXECUTIVE ASSISTANT - Real Estate Business

THIS IS NOT A TRADITIONAL VA ROLE. Seeking someone who is looking for a long term stable job for 4+ years minimum. We are seeking an exceptional Executive Business Assistant to work directly with a fast-moving entrepreneur across multiple businesses, including residential real estate, short-term rentals, personal-brand marketing, and business administration. This person will become the operational right hand behind the businesses: highly organized, technically capable, resourceful, thoughtful, and unusually strong at follow-through. The right person does not wait to be handed a perfect checklist. They listen closely, recognize what needs to happen next, build the plan, execute it, verify that it worked, and communicate the outcome. They bring completed solutions whenever possible—not a growing list of problems for someone else to resolve. This role is ideal for someone who genuinely enjoys creating order, serving an entrepreneur at a high level, mastering new systems, and becoming the person everyone can trust to close the loop. What Success Looks Like Tasks discussed in meetings or conversations are captured, scheduled, completed, and reported back without repeated reminders. Recurring daily, weekly, monthly, and annual responsibilities happen on time because you have built and maintain the operating rhythm. Automations, forms, websites, and workflows are not merely built—they are tested end to end, monitored, and corrected when necessary. Problems are investigated independently. You use sound judgment, present a recommendation when approval is needed, and otherwise resolve the matter within your authority. Communication is proactive and concise: what happened, what you did, what is complete, and what—if anything—is still needed. The executive feels prepared rather than surprised, and rarely needs to ask twice or check whether something was finished. Core Responsibilities Executive Support & Operational Ownership Manage appointments, reminders, follow-ups, deadlines, registrations, renewals, and routine administrative details across multiple businesses. Attend or review meetings as requested, internalize the discussion, identify commitments and next actions, assign due dates, and follow each item through completion. Respond to routine emails professionally, organize communications, follow up with vendors and partners, and ensure open loops do not disappear. Make approved small purchases, including supplies and replacement items for short-term rentals. Build repeatable checklists, dashboards, SOPs, and recurring task systems so important work does not depend on memory. Communicate progress without being chased and escalate only when a decision, material risk, or executive authority is genuinely required. Real Estate Operations Prepare MLS listing materials and coordinate the administrative steps required to launch and maintain listings. Schedule and promote open houses; coordinate calendars, vendors, marketing assets, and follow-up. Support social-media publishing for real estate content. Maintain a sphere-of-influence CRM, including gifting, important dates, routine communication, database cleanup, and follow-up workflows. Prepare and send polished weekly update emails to listing clients using information provided by the team. Create alerts, track listing-related deadlines, and ensure client and property follow-ups are completed. Short-Term Rental / VRBO Operations Handle routine guest calls and messages with warmth, speed, and good judgment; escalate emergencies or sensitive issues appropriately. Manage calendar blocks and availability in Hostaway and connected platforms. Coordinate maintenance, repairs, cleaning-related needs, supplies, and vendor access. Track recurring services such as lawn care and hot-tub cleaning and provide timely payment reminders or invoice support. Place approved property-supply orders and confirm delivery and resolution. Identify recurring guest or property issues and recommend a process, automation, or preventive fix. Marketing, Content Production & Publishing Turn approved messaging into polished email-marketing campaigns and newsletters, format them, test every link and display, schedule them, and confirm successful delivery. Create high-quality Canva graphics, Instagram Stories, and short-form video assets efficiently and consistently. Publish approved content across designated platforms with accurate captions, links, tags, timing, and formatting. Help build a practical 30-day-ahead Reel pipeline: research relevant formats, organize ideas, recommend videos to replicate, prepare recording instructions, and make filming easy for the executive. Track the content calendar and ensure approved assets move from idea to recording, editing, review, scheduling, and publication. Monitor basic performance data and recommend practical improvements based on what is working. Systems, Automation & Digital Operations Build, maintain, and troubleshoot GoHighLevel workflows, triggers, pipelines, forms, campaigns, and follow-up sequences. Create and manage Instagram keyword responders and connected lead-capture workflows. Pull, clean, organize, and validate data lists for marketing and operational projects. Update and edit websites, landing pages, forms, and basic content while protecting brand consistency and user experience. Test every automation from the end user's perspective, confirm data lands in the correct system, check notifications and follow-ups, and document the final configuration. Use AI thoughtfully to accelerate recurring work, including invoice allocation, drafting, research, documentation, and quality control—without sacrificing accuracy. Bookkeeping Coordination Gather and organize invoices, receipts, and supporting records across multiple businesses each month. Identify which company or property should be billed, flag missing information, and maintain an orderly approval process. Coordinate with bookkeepers, vendors, and internal stakeholders so documents and answers arrive on time. Develop repeatable and, where practical, AI-assisted processes for recurring invoice coding and allocation, subject to review and financial controls. This position coordinates financial administration; it does not independently provide accounting advice or authorize unapproved material payments. The Standard: How You Work Anticipate: Think several steps ahead. Ask: What will be needed next? What could fall through? What can I prepare now? Own: If you accept a task, you own the outcome—including follow-up, quality control, and communication. Solve: Research first. Use available resources. Try sensible solutions. Bring context and a recommendation when a decision is required. Verify: Never assume a setup worked. Test links, forms, workflows, scheduling, delivery, permissions, and the final user experience. Close the loop: Confirm completion, summarize the result, record relevant details, and identify any next step. Silence is not a status update. Move with speed: Work with urgency while maintaining accuracy. Distinguish between reversible decisions you can make and material decisions that require approval. Communicate early: If internet, power, health, or another disruption affects availability, notify the executive promptly through WhatsApp and share the recovery plan or estimated return time. Required Qualifications Exceptional written English and clear, highly proficient spoken English that is easily understood by U.S. clients, guests, vendors, and partners. Demonstrated success supporting a busy entrepreneur, founder, executive, or multi-business owner in a high-accountability environment. Advanced Canva skills and strong short-form video editing ability for Reels and Stories. Hands-on GoHighLevel experience, including building and troubleshooting automations and follow-up workflows. Experience with real estate operations or MLS processes and short-term-rental operations; direct experience in both is strongly preferred. Strong technology and AI fluency, with the ability to learn unfamiliar software independently and quickly. Excellent judgment, organization, prioritization, documentation, and deadline management. High responsiveness and reliable availability throughout 9:00 a.m.–5:00 p.m. Eastern, with occasional evening or weekend availability when genuinely needed. A long-term mindset, high discretion, and the maturity to handle confidential business and personal information. Professional workspace, modern computer, fast and reliable primary internet, backup internet, and a realistic contingency plan for power outages or other local disruptions. Preferred Tools & Experience GoHighLevel • Canva • Instagram and Meta tools • Hostaway • VRBO / Airbnb host operations • MLS platforms • CRM systems • email-marketing platforms • Google Workspace • task/project-management systems • website builders/CMS tools • AI productivity tools You do not need to know every tool on day one, but you must be confident learning new systems without requiring step-by-step instruction for every feature. Decision-Making & Escalation You will have room to execute routine, reversible, and previously approved actions independently. The executive should be consulted before material financial commitments, sensitive client or guest decisions, legal or compliance matters, major changes to brand messaging, or actions with meaningful reputational risk. A STRONG ESCALATION SOUNDS LIKE: “Here is what happened, what I checked, the options I found, my recommendation, the cost or risk, and the decision I need from you by this time.” Role Details Engagement: Full-time independent contractor Location: Remote; applicants may be based globally Core hours: 9:00 a.m.–5:00 p.m. Eastern Time, consistently Availability: Occasional evenings or weekends when business needs require Target start: August 1, 2026 Commitment: Long-term relationship preferred How to Apply - Please submit the following: A short introduction explaining why this specific role fits the way you work. A résumé or detailed summary of relevant executive-support, real estate, rental, marketing, and automation experience. Examples of Canva designs, Reels/Stories, email campaigns, websites, or GoHighLevel sites or workflows you personally created. A 60–90 second video introduction so we can evaluate communication style and spoken-English clarity. Your location, time zone, requested monthly rate in USD, internet speed-test result, computer specifications, and backup internet/power plan. A response to this scenario: You build a lead workflow and the test contact does not receive the SMS. Explain exactly what you would do next and how you would report the outcome. Applications that do not follow these instructions may not be considered.