Executive Operations Assistant (Property Management | STR + LTR | Systems-Focused)

Executive Operations Assistant (Property Management | STR + LTR | Systems-Focused)

We are hiring ONE highly organized, tech-savvy Executive Operations Assistant with proven experience supporting executives and managing operations for both short-term and long-term rental portfolios. Reply Eastern hours to this job post if your able to work that time zone. Please attach your Resume when apply for this job opportunity.

This is NOT a basic VA role.
You must have real administrative depth, executive support experience, and strong operational systems thinking.

What You Will Own:

Executive calendar management & scheduling


Email management and inbox organization

Administrative oversight and task prioritization

Daily operations for STR and LTR properties

Vendor coordination & maintenance tracking

Tenant and guest communication management

Digital file organization (invoices, receipts, contracts)

Support bookkeeping workflows (QuickBooks Online preferred)

Work inside property management software (Buildium, OwnerRez, etc.)

Improve workflows and implement automation where possible

Light social media support (Instagram, Facebook, TikTok)

Required Experience (Non-Negotiable):

Proven Executive Assistant experience (supporting leadership directly)

Strong administrative background (not just task-based VA work)

Experience managing STR and LTR property operations

Exceptional time management & ability to prioritize independently

Extremely organized with digital file systems

Highly tech-savvy and fast with new software

Comfortable using multiple platforms daily

Strong written communication skills

Proactive problem-solver who stays ahead of issues

This Role Is For Someone Who:

Thinks in systems

Creates structure

Manages time efficiently without supervision

Improves processes instead of just following instructions

Long-term role. Growth opportunity for the right candidate.