Operations & Property Management Specialist

Remote - Full-Time | Short-Term & Midterm Rental Portfolio

About the Role

We're a fast-growing short-term and midterm rental operation managing 50+ furnished properties, including luxury hospitality homes near a major golf tournament destination and a large multi-unit furnished housing community. We're looking for a senior, hands-on Operations & Property Management Specialist to work directly alongside the owner, take ownership of daily guest and tenant communications, and help transform years of “in-the-owner’s-head” processes into documented, repeatable systems.

This is not a generalist VA role and not a “busy work” position. You'll be the right hand to a solo operator who has built a 50+ door portfolio from the ground up and needs someone who can absorb real operational responsibility quickly, managing reservations, guest messaging, maintenance coordination, and vendor communication from day one, while documenting everything into SOPs and training materials that future team members will use.

What You'll Do

• Manage day-to-day guest communications across Lodgify, Airbnb, Booking.com, and other channels, inquiries, reservations, extensions, and check-in/check-out coordination

• Respond to cold inbound leads from Facebook, Furnished Finder, and other listing platforms

• Coordinate with the cleaning and maintenance teams via Turno, assigning turnovers, confirming completions, and tracking maintenance requests through to resolution

• Build and maintain a maintenance triage system (e.g., “if AC isn't working, do X”) so requests are handled consistently without relying on the owner

• Own the company's social media presence and Google Business Profile, regular posting, staying active/relevant, and proactively requesting guest reviews

• Document existing processes into SOPs using Notion, capturing workflows the owner currently manages from memory and scattered Trello cards

• Create training videos (Loom) for each documented process, building a library that future hires will use for onboarding

• Participate in daily live-training sessions with the owner during the initial ramp-up period shadowing real guest messages, reservations, and maintenance calls to learn systems in real time

• Help evaluate and implement tools like PriceLabs for dynamic pricing across the portfolio

• Over time, take ownership of an increasing share of daily operations so the owner can step back from day-to-day messaging and admin

What We're Looking For

• 3+ years of experience in property management, short-term rental operations, or a comparable operations/SDR role

• Fluent in both Spanish and English (written and verbal) this is a hard requirement given the team's vendor and ownership communication

• Comfortable working U.S. business hours with strong overlap for live daily training in the first 60-90 days

• Experience with short-term rental property management software (Lodgify, Turno, Hostaway, Guesty, or similar) is a strong plus

• Experience with Notion (or similar tools like Asana) for building structured documentation and SOPs

• Self-directed and comfortable taking ownership without close supervision, someone who “just runs with it” once trained

• Strong written communication, you'll be the voice of the business to guests, tenants, and vendors

• A systems-thinker: someone who naturally documents, organizes, and improves processes rather than just executing tasks

• Experience supporting a high-volume portfolio (multiple properties/units) is highly preferred

How Success Looks in the First 90 Days

• You've completed daily live training sessions with the owner and can independently handle guest messaging, reservations, and basic maintenance triage

• Core workflows (guest communication, turnovers, maintenance escalation, review requests) are documented in Notion with accompanying Loom walkthroughs

• The owner has measurably fewer inbound messages requiring their direct attention

• A clear onboarding framework exists that the next hire can use to ramp up quickly

Why Join This Team

• Work directly with a hands-on owner-operator with 300+ completed renovation projects and a fast-growing rental portfolio

• Be the foundational hire for an operations team that's actively scaling strong potential for growth into a leadership role over future hires

• Fully remote, with flexibility once systems are in place

• Exposure to real estate, hospitality, and property management operations at scale