AI-Augmented Executive Assistant – Real Estate Investment & Short-Term Rental Operator

Job Description: Overview: I am seeking an elite, systems-driven Executive Virtual Assistant to serve as an operational partner across three core areas: executive personal branding on LinkedIn (Commercial Real Estate/Lending focus), Short-Term Rental (STR) portfolio logistics, and sensitive financial administrative workflows. This is not a traditional data entry role. I am looking for a highly tech-forward operator who actively leverages modern AI productivity stacks (ChatGPT/Claude, Taplio, Zapier/Make) to multiply their own output while maintaining flawless execution and absolute data security. Core Responsibilities: 1. Professional Branding & LinkedIn Management Content Operations: Leverage AI tools (e.g., Taplio, Supergrow) to draft 3 high-quality, authoritative professional posts per week focused on macroeconomics, underwriting, and commercial real estate trends. Media Creation: Repurpose complex text, regulatory updates, or financial trends into highly visual, scannable PDF mobile carousels. Inbox & Engagement Triage: Dedicate 15 minutes daily to organic networking and comment management. Audit the direct message inbox to filter out automation spam, highlighting only high-value professional opportunities. 2. Short-Term Rental Portfolio Logistics Guest Experience Operations: Oversee automated messaging frameworks within our Property Management Software (Hospitable/Hostaway). Step in manually to handle complex inquiries, custom booking updates, and guest resolution. Turnover Logistics: Cross-reference checkout data with cleaning schedules to ensure seamless turnovers across distinct regional properties (including coastal and mountain markets). Verify turnover completion via photos. Vendor Dispatch: Act as the primary coordinator for maintenance issues, managing communications with local technicians and tracking repairs through to resolution. 3. Financial Admin, Spreadsheets & Personal Errands Spreadsheet Management: Log recurring property bills, utility statements, and construction invoices into active portfolio spreadsheets. Maintain pristine data hygiene to match strict cash-on-cash underwriting targets. Tax Document Tracking: Systematically organize and file asset improvement receipts to support ongoing cost segregation and capital improvement tracking. Personal Billing & Admin Support: Efficiently track recurring corporate/personal bill cycles, coordinate payment updates, and manage premium travel or rewards logistical data entry. Required Profile & Technical Competencies: Experience: 2+ years of experience supporting executives, real estate investors, or managing boutique hospitality portfolios. AI Stack Fluency: Deep, hands-on experience prompting and editing with ChatGPT/Claude, LinkedIn growth tools (Taplio/Supergrow), and property channel managers (Hospitable, Hostaway, or Guesty). Analytical Skills: High intermediate proficiency with Microsoft Excel / Google Sheets (formulas, lookup functions, structured data tables). Exceptional attention to detail when auditing numbers. Communication: Elite verbal and written English with a polished, professional, and corporate tone. Time Zone Alignment: Must be available to work and monitor operations during US Eastern Time (ET) business hours. Security Mindset: Absolute discretion and familiarity with secure data sharing practices (1Password, multi-factor authentication protocols). How to Apply: To be considered for this role, please reply with a cover letter that directly addresses the following: What specific AI or automation stack do you currently use to streamline content creation or property management operations? Briefly describe your experience managing a short-term rental checkout or maintenance crisis. Important: Please start the very first line of your response with the words "System Operator Found" so I know you have thoroughly read this entire scope of work.