We are a Chicago-based furnished rental business operating a portfolio of short-term and midterm rental units (32+ night stays) in one of the city's most dynamic neighborhoods. Our properties are thoughtfully designed, impeccably maintained, and managed with a hospitality-first mindset — our guests expect hotel-quality standards, and we deliver. As we scale from 4 to 8 units, we are looking for a dedicated Virtual Assistant to become the operational backbone of our guest experience and property logistics.
This is not a passive role. You will own the guest communication pipeline, coordinate our cleaning and turnover crews, manage linen staging logistics, and help us build systems that scale. You will also play a key role in building out our direct-booking website — reducing our reliance on third-party platforms and giving guests a richer, more transparent way to discover our properties.
We are a small, tight-knit team with deep roots in the Chicago Latino community. We value hard work, loyalty, and the kind of ownership mentality that means you don't freeze when something unexpected comes up — you solve it, communicate it, and keep things moving. If you are bilingual (English/Spanish), highly organized, and ready to grow with a fast-moving hospitality business, we want to hear from you.
• Guest Communication & Issue Resolution — Serve as the first point of contact for all guest inquiries, requests, and concerns via Airbnb messaging. Handle day-to-day communication professionally and proactively, using good judgment to resolve issues independently where possible and escalating to the owner when in-person intervention is needed.
• Cleaning Crew Coordination & Vetting — Schedule and coordinate cleaning crews for all unit turnovers. Vet and onboard new cleaners as needed, maintain consistent quality standards, and ensure the right team is assigned to each unit for every turnover. Build and maintain a reliable bench of cleaning partners.
• Turnover & Linen Logistics Management — Manage the full sequence of events between guest stays: confirm checkout/check-in times, coordinate linen staging and restocking of guest supplies (soaps, consumables), and ensure cleaners have everything they need before arriving on site. Build and refine a turnover checklist system that minimizes the owner's need for in-person oversight.
• Direct Booking Website Support — Assist in building and maintaining a direct-booking website (Squarespace or similar platform — no coding required). Help create and upload property content including listing descriptions, photos, and iPhone video walkthroughs. Support efforts to migrate Airbnb inquiries toward the direct-booking platform over time.
• General Operations & Administrative Support — Support day-to-day operational tasks including vendor communication, research (cleaning services, suppliers, tools), basic document and presentation preparation, and other ad-hoc tasks as the business grows. Be available, responsive, and proactive in flagging anything that needs the owner's attention.
Required:
• Fluent English communication skills (written and verbal) — you will be the voice of our brand to guests
• Bilingual English/Spanish strongly preferred — our team and many of our vendor relationships are Spanish-speaking
• Strong problem-solving mindset — you can navigate unexpected situations without waiting to be told what to do
• High conscientiousness and reliability — you follow through, meet deadlines, and keep commitments
• Tech-savvy with common tools (Google Suite, Airbnb platform, Squarespace or similar website builders, basic design/presentation tools)
• Available during US Central (Chicago) business hours; responsive to time-sensitive guest needs
• Full-time or part-time availability with consistent weekly commitment (20–40 hrs/week based on agreement)
• Located in Latin America or Philippines — we are open to both
• Experience in short-term rental or property management operations
• Familiarity with Airbnb host tools, pricing, or listing management
• Prior experience supporting a US-based client
• Experience with video content creation or uploading (even basic iPhone video editing)
• Demonstrated examples of digital work — websites, dashboards, presentations, or online listings you have contributed to
• Hours: Part-time (20 hrs/week) to start, with clear path to full-time (40 hrs/week)
• Schedule: Flexible, with availability during US Central (Chicago) business hours; Sunday availability not required
• Work Arrangement: 100% Remote
• Compensation: $550–$600 USD/month (part-time) | $1,100–$1,200 USD/month (full-time)
• Engagement Type: Independent Contractor
• Location: Latin America (preferred) or Philippines
Facebook: facebook.com/ltg.assist
Instagram: instagram.com/ltg_assist
Check out our open positions here: ltginvestments.com/careers
Facebook: facebook.com/ltg.assist | Instagram: instagram.com/ltg_assist
Check out our open positions here: ltginvestments.com/careers