Maintenance Technician - Short Term Rentals

What we do and why we do it

As the leading end-to-end investment platform for single-family rental homes, our mission is to make real estate investing radically accessible, cost effective, and simple. Our short-term rental (STR) business extends this mission into hospitality, delivering seamless guest experiences while maximizing returns for homeowners.

How it’s going (and growing)

With a talented team of 750+ Roofsters, our collaborative, can-do culture is what fuels our growth. In 2022, we closed on our Series E, raising $240 million, and have offices in the Bay Area and New York City. Our growth includes recent acquisitions of Stessa (financial and asset management software), RentPrep (tenant screening and placement service for landlords), and Mynd (property management platform for both Retail and Institutional investors). In 2025, Roofstock took an ownership stake in Casago (short-term rental management services), expanding our platform to support both long-term and short-term rental investment services.

Roofstock’s Values → Short-Term Rental (STR) Org Reflection

• We are entrepreneurs → Launch a startup within a startup● We are better together → Work across functions and markets to do it fast and well● We focus on impact → Build a profitable business unit with satisfied owners, teammates, and guests● We think like investors → Protect owners’ homes and maximize ROI

About the Role

As a Maintenance Technician for short-term rentals, you’ll play a key role in ensuring our homes are functional, clean, and stocked (FCS), safe, and guest-ready. You’ll respond to urgent in-stay needs, perform routine inspections and preventative maintenance, and work closely with the Team Lead, Back of House and Back of House Coordinator to manage tasks, supplies, and vendor relationships.

This role requires a well-rounded maintenance skillset and a service mindset. You’ll be part of the local Back of House team and work across multiple homes within your assigned market.

Responsibilities

• Complete preventative and routine maintenance tasks, including HVAC troubleshooting, appliance repair, light plumbing and electrical work, and basic cable/Wi-Fi resets
• Respond promptly to guest-reported issues during stays, resolving them quickly and professionally
• Support turnovers and readiness work, including light patching, assembly, and touch-ups
• Conduct property inspections to identify and document potential issues before they impact the guest experience
• Coordinate with the Back of House Coordinator on inventory, work orders, vendor support, and scheduling
• Communicate professionally with the Team Lead, Back of House and other local team members
• Ensure documentation is accurate and submitted in a timely manner for each job completed
• Follow brand and safety standards in every home
• Collaborate with Hospitality Ops team members to ensure homes meet FCS expectations
• Other duties as assigned

Qualifications

• 3+ years of maintenance experience, ideally in hospitality, vacation rental, or residential property management
• Strong troubleshooting and problem-solving skills across multiple home systems
• HVAC Type II Certification preferred
• Familiarity with digital work order systems and mobile task apps
• Valid driver’s license and reliable transportation required
• Calm, professional demeanor with a customer service mindset
• Able to work evenings, weekends, and participate in on-call rotation
• Comfortable with physically demanding work and frequent travel between homes

Location – Charleston, SC

Travel Required

Regular travel between properties within the local market.

Competitive & Unique Benefits Package

• Generous PTO Policy
• 12 Paid Holidays
• Volunteer Time Off
• Paid Parental Leave
• 401k Program
• Health, dental, vision insurance, and more
• Work & Wellness Stipend as $100/month for tools and equipment

Must be authorized to work in the U.S. is a precondition of employment and we are unable to sponsor H1-B Visas at this time. 

Any offer of employment is conditioned upon the successful completion of a background investigation.  

Commitment to Equal Employment Opportunity

Roofstock provides equal opportunity in all of our employment practices to all qualified employees and applicants without regard to race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, or any other protected status.

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