Operations Manager / Property Management Assistant

ABOUT THE ROLE

We are sourcing on behalf of a high-growth Miami-based real estate investor who self-manages a portfolio of 100+ doors - spanning long-term Section 8 multifamily buildings, high-end Airbnb properties, and everything in between. The portfolio is expanding fast (next target: 1,000 doors), and the owner needs a sharp, experienced right-hand person who can take operational chaos off their plate permanently.
This is not a task-runner role. You will be trusted to problem-solve, communicate with city officials, lenders, insurance companies, tenants, and contractors - often independently. Mistakes here cost money and relationships. The ideal candidate has seen it all before and knows what to do without being told.

WHAT YOU'LL OWN
• Manage all inbound communications: emails from lenders, insurance companies, city agencies, tenants, utility providers, and vendors
• Handle Appfolio day-to-day: tenant records, lease tracking, document uploads, maintenance requests
• Coordinate short-term rental operations across 2 high-value STR properties: guest communications, Airbnb/VRBO workflows, pricing optimization via PriceLabs, and platform integrations (HostAway/Guesty setup and management)
• Track and respond to city violations, permits, and municipal deadlines - knowing exactly what to say and what not to say
• Support the acquisition pipeline: coordinate with lenders, title companies, appraisers, inspectors, and environmental teams during purchases and refinances
• Oversee insurance policy renewals, lender requirements, and compliance documentation
• Track rent collection, flag delinquencies, and liaise with Section 8 caseworkers
• Source and coordinate contractors and vendors; follow up on maintenance and turnover work
• Build and maintain SOPs to create a scalable, organized operation
• Handle utility setups, trash services, permit applications, and other administrative follow through

MUST-HAVE EXPERIENCE
• 3+ years in property management, real estate operations, or a closely related role
• Strong Appfolio experience: tenant management, lease uploads, maintenance ticketing
• Section 8 / HUD housing: tenant screening, caseworker communication, compliance
• Airbnb, VRBO, and STR guest communication: message cadences, dispute resolution, platform policies
• PriceLabs or similar dynamic pricing tools
• HostAway, Guesty, or similar channel management/PMS platforms (or strong readiness to implement)
• Experience interfacing with government offices, lenders, and insurance carriers
• Fluent English (written and verbal) - bilingual English/Spanish strongly preferred

WHAT MAKES YOU STAND OUT
• You proofread everything before it goes out - errors are not something you make twice
• You've worked directly for a founder, investor, or executive in a high-stakes environment
• You know how to talk to the city, what to disclose, and what to stay quiet about
• You're a problem-solver, not just a task-completor - you identify issues and come to the table with solutions
• You understand that 2% of this portfolio is STR but it's 100% a pain point, and you treat it accordingly