Upstay is looking for a Full Time Assistant Maintenance Manager to join our team in Orlando, Florida! Get Your Resume Ready! Who We Are Upstay.com is a tech-enabled hospitality company that designs and manages every aspect of our guests' stay to ensure an exceptional experience. Since launching, our team has rapidly grown to over 100+ employees operating 300+ homes in the United States, Mexico, Colombia, and Canada. Joining Upstay will provide you with the unique chance to join a high-growth start-up and explore new opportunities in a collaborative and inclusive environment. What We Do We build great communities that bring the tools and sensibilities of the world's best hotels and apply these principles to our vacation rentals, short-term rentals, and modern hotels. How We Do It We are accountable for every aspect of our property's creation and existence. Site selection, acquisition, development, design, construction, furniture manufacturing, laundry and property management are all looked after by our in-house teams which translates to higher standards in our properties, service, and customer expectations. What Matters to Us We are committed to providing compliant and locally beneficial short-term property rentals that add value to our guests. We work with local governments and homeowner associations to develop standards and provide industry-wide leadership so our guests can relax and enjoy their time with us. Learn more at www.upstay.com. The Assistant Maintenance Manager supports day-to-day maintenance operations, technician coordination, quality control, vendor management, property inspections, training, and administrative reporting. Working alongside the Maintenance Manager, Superhosts, Cleaning Partners, Maintenance Technicians, and external vendors, this role supports all operational and maintenance efforts to ensure products and services delivered meet Upstay standards.

What You'll Do:

Maintenance Operations & Task Execution Use Breezeway to receive, start, prioritize, track, and complete assigned work orders in a timely manner. Support Maintenance Technicians in daily tasks, troubleshooting, repairs, and scheduled preventative maintenance. Assist with hands-on maintenance activities when operationally required. Help prioritize maintenance needs based on urgency, guest impact, property condition, and operational priorities. Address or coordinate emergency maintenance escalations during guest stays, including plumbing leaks, HVAC failures, smart-lock issues, Wi-Fi outages, appliance failures, and other urgent property concerns. Ensure maintenance work is properly documented before work orders are closed. Maintain an organized inventory of essential spare parts, hardware, smart-home devices, tools, and maintenance supplies. Team Leadership & Accountability Support the Maintenance Manager in coordinating and supervising the day-to-day activities of Maintenance Technicians. Help assign and prioritize work based on operational needs and technician availability. Follow up on overdue or incomplete work orders and verify that assigned tasks are completed according to Upstay standards. Track technician productivity and work-order completion. Identify performance gaps or recurring issues and support the Maintenance Manager with coaching, corrective follow-up, and documentation when required. Attend and actively contribute to daily/weekly operations meetings, stand-ups, and maintenance planning sessions. Communicate priorities, blockers, property concerns, and operational updates between field technicians and management. Superhost & Property Onboarding Support Work with Superhosts to prioritize maintenance needs during the SuperHost onboarding period. Identify, document, and prioritize initial punch-list items and maintenance needs before properties go live. Coordinate with relevant teams to ensure maintenance concerns affecting property readiness are addressed promptly. Support operational efforts to ensure newly onboarded properties meet Upstay standards.

What You'll Bring:

Experience:

2+ year of proven residential maintenance experience, preferably within hotels, Airbnb, vacation rentals, or short-term rental operations. Previous experience coordinating or supervising maintenance technicians, contractors, or operational teams is an asset.

Education:

High school diploma or similar technical/vocational certification.

Systems:

Familiarity with PMS and property operations systems, with Guesty and Breezeway preferred. Comfortable using Slack, email, Google Sheets, and/or Microsoft Excel. Basic understanding of repair costs, vendor quotes, maintenance scopes, and expense tracking. Available to work flexible shifts, including days, evenings, weekends, and holidays. Days off are during the week; work is required on Saturdays and Sundays. Must have a reliable vehicle and valid driver's licence. Transportation between properties must be done using your own vehicle; the company does not provide one. Fluent written and oral English is required. Spanish or Portuguese language skills are good to have. Must be physically fit to lift heavy products or materials up to 50+ lbs. on a regular basis. Must be able to bend, climb stairs, use ladders, and perform hands-on maintenance activities as required.

Equal Employment Opportunity:

We're proud to be an equal opportunity employer and all applicants will be considered. At Upstay we celebrate and support the differences between our employees' including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, and Veteran status. Diversity is essential to our growth, and we've concluded that we're stronger together.

Last Thing:

If this isn't the job for you, perhaps you have a friend who would be a perfect fit? Send them this job posting.

Job Type:

Full-time Pay:

$48,000.00 - $50,000.00 per year

Experience:

Property maintenance: 2 years (Required)

Management:

1 year (Preferred)

License/Certification:

Drivers license (Required)

Work Location:

In person