Executive Assistant / Virtual Assistant for Real Estate & Business Operations

The client operates a real estate and construction business with a rental portfolio of roughly 50 properties, managed through a mix of about 7 external property managers and some units he oversees directly. He also has active new-construction projects, is acquiring a franchise (101 Mobility — mobility ramps and lifts), and is setting up a recording studio. This is his first time hiring support, and he needs someone to take ownership of recurring admin and communications so he can focus on the business.

Key Responsibilities

• Track mortgage payments across the rental property portfolio and follow up to keep everything current.
• Monitor rent payments for self-managed tenants; flag late or missing payments and escalate appropriately (e.g., routing to eviction process when needed).
• Keep organized records (currently Google Sheets) across ~7 property managers and ~50 rental units.
• Manage Rob's email inbox — organize, label, and respond on his behalf where appropriate.
• Manage his calendar and scheduling.
• Make and take phone calls with vendors, utility providers, and servicers — e.g., setting up/tearing down utilities between tenants on construction turnovers.
• Provide general executive assistant support across Rob's ventures (construction, property management, franchise acquisition, recording studio) — the day-to-day mix will be varied and ad hoc.
• Help coordinate documentation and next steps with outside professionals (e.g., tax structuring) — not performing the work itself, but keeping it moving.
• Help build out a simple, reliable tracking system for tenant and mortgage payments, with an eye toward adopting dedicated software down the line.

What We're Looking For

• Prior experience as a VA or EA, ideally with exposure to real estate, property management, or small business operations.
• Comfortable making and taking phone calls with vendors and service providers.
• Highly organized and able to manage multiple, sometimes competing priorities for one busy principal.
• Proficient in Google Workspace (Sheets, Gmail, Calendar).
• Discreet and dependable — this role touches sensitive financial information (rent, mortgages, credit-related matters).
• Comfortable with ambiguity — the role is still taking shape and will evolve as the working relationship develops.
• Able to work Eastern Time hours.