--- title: 'Short-term Rental Home Inspector (1099) at Roofstock' canonical: 'https://feeny.ai/job/short-term-rental-home-inspector-1099-roofstock-rockaway-beach-oregon-g6k8rt4va2bp' type: 'job' last_seen: '2026-09-16' --- # Short-term Rental Home Inspector (1099) at Roofstock - **Company:** Roofstock - **Location:** Rockaway Beach Oregon, United States - **Posted:** 2026-06-23 - **Last confirmed live:** 2026-09-16 - **Apply:** https://job-boards.greenhouse.io/roofstock/jobs/8604291002 ## Job description Short-term Rental Home Inspector (1099) Location: Rockaway Beach, OR Type: Independent Contractor ## Overview Seeking independent contractors to support short-term rental homes with inspections, light prep, and in-market assistance between guest stays. Services May Include - Pre/post-stay inspections - Light home resets and restocking - Minor maintenance tasks - Turnover support and trash removal - Responding to urgent on-site issues - Task updates via mobile app Ideal Contractor - Experience in hospitality, vacation rentals, or property care - Reliable vehicle and smartphone - Able to work independently and manage availability - Comfortable with light physical work - Weekend availability preferred Engagement Details - 1099 independent contractor (not employment or benefits eligible) - Flexible, task-based work - Contractor responsible for taxes and insurance Compensation: $22.50/hour, with the option for per-task/piece-work pay for experienced contractors. We are open to discussing a flat rate per inspection/job. Apply to join our local contractor network. ## About Roofstock ## Company Overview - **One-liner**: Roofstock provides an end-to-end investment platform for single-family rental (SFR) homes, allowing investors to buy, manage, and sell properties with data-driven tools and professional services. - **Entity Type**: Private (Series E) - **Headquarters**: Oakland, California, USA (also offices in New York City and Buffalo, NY) - **Founded**: 2015 - **Founders**: Gary Beasley, Doug Brien, Devin Wade, Gregor Watson, Rich Ford ## Core Business - **Primary industry**: Real estate technology (fintech focused on single-family rentals) - **Target customers**: B2B and B2C – individual investors (retail) to institutional investors, property managers, and landlords. - **Mission or purpose statement**: "Better investing, better housing" – to reinvent the rental housing ecosystem for the benefit of all, helping investors own and operate quality rentals in communities people want to call home. ## Products & Services - **Acquisitions**: A marketplace to confidently deploy capital into SFR properties with certified listings and analytics. - **Asset Management**: Portfolio performance monitoring, issue tracking, and expert guidance to optimize returns. - **Property Management** (powered by Mynd): Full-service management for individual and institutional investors. - **Tenant Screening** (RentPrep): FCRA-certified screening to reduce tenant risk. - **Portfolio Management Software** (Stessa): Easy-to-use software for landlords to manage finances and assets. - **Dispositions**: Exit single assets, whole portfolios, or a combination. - **Roofstock onChain**: Facilitated the first NFT-based single-family property sale. - **Short-term rental services** (via stake in Casago, 2025): Expansion into short-term rental management. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed - **Key Metric**: Total Funding – $240 million (Series E, closed 2022) - **Notable Investors/Partners**: Bain Capital, Khosla Ventures, Ron Conway, Marc Benioff; also listed on Forbes Fintech 50 (2022), CB Insights Fintech 250 (2022), HousingWire Tech 100 (2023) - **Growth Signals**: - Over $10B transacted, 400K+ units, 800+ employees (known as "Roofsters") - Merged with Mynd (2024); acquired RentPrep, Stessa, Streetlane Homes, Great Jones; took ownership stake in Casago (2025) - Named Best Workplace for women, tech, and millennials (2022) - Recognized for forging the way in fintech and blockchain real estate ## Competitive Advantages - **End-to-end platform**: Covers acquisition, property management, tenant screening, asset management, and disposition – all in one place. - **Scattered-site SFR technology**: Built specifically for the complexities of managing rental homes across different neighborhoods. - **Experienced leadership**: Founders previously built Waypoint Homes (took public on NYSE) and Mynd; deep domain expertise in SFR as an asset class. - **Data-driven approach**: Uses FCRA-certified screening and portfolio analytics to drive returns. - **Strategic acquisitions**: Rapidly integrated complementary services to create a unified ecosystem. ## Strategic Focus - **Expand platform breadth**: Support both long-term and short-term rental investment services (via Casago). - **Serve all investor segments**: From individual landlords to institutions, with tailored offerings. - **Continue technology innovation**: Leverage blockchain for property tokenization and invest in software that increases portfolio transparency. - **Scale operations**: Grow headcount (currently 750–800+ employees) and geographic footprint (offices in California, New York, North Carolina, Texas, Georgia). ## Why Work Here - **Culture highlights**: Valued for being entrepreneurial, making an impact, thinking like investors, and being better together. Emphasis on diversity, inclusion, and "being you". Recognized as a best workplace. - **Remote/hybrid/office policy**: Multiple office locations (Oakland, NYC, Buffalo, Atlanta, Charlotte, Dallas) and remote roles available (e.g., Resident Experience Manager). Hybrid likely; specific policy not stated. - **Notable perks and benefits**: - Health insurance (up to 100% premium coverage) - Equity incentives and competitive pay - 401k with retirement savings options - Flexible time off and wellness programs - Thorough onboarding with swag - **Engineering culture**: Technology-driven company with a focus on building the future of real estate; CTO Lloyd Hsu leads engineering. Innovation is prized. ## Sources 1. [Roofstock Careers Page](https://www.roofstock.com/company/careers) 2. [Roofstock Main Website](https://www.roofstock.com/) 3. [Roofstock About Page](https://www.roofstock.com/about-us) 4. [Roofstock Greenhouse Jobs Page](http://job-boards.greenhouse.io/roofstock) 5. [Crunchbase Roofstock Profile](https://www.crunchbase.com/organization/roofstock) ## Other roles at Roofstock - [Senior Property Accountant, Institutional](https://feeny.ai/job/senior-property-accountant-institutional-roofstock-dallas-texas-8fgfkhwgtqv8) — Dallas Texas, United States - [Property Accountant, Institutional](https://feeny.ai/job/property-accountant-institutional-roofstock-dallas-texas-8n1zr7bb9ghx) — Dallas Texas, United States - [Senior Product Manager, Leasing](https://feeny.ai/job/senior-product-manager-leasing-roofstock-new-york-c5nyx8rt2mgj) — New York, NY / Oakland California, United States - [Service Technician](https://feeny.ai/job/service-technician-roofstock-sacramento-california-0js2xx63r56e) — Sacramento California, United States - [Property Inspector](https://feeny.ai/job/property-inspector-roofstock-pacific-city-oregon-nzhv50kby9sh) — Pacific City Oregon, United States - [Supervisor, Hospitality Operations](https://feeny.ai/job/supervisor-hospitality-operations-roofstock-oceanside-oregon-0sb3rnf0fqyv) — Oceanside Oregon, United States - [Piecework Housekeeper - Part Time](https://feeny.ai/job/piecework-housekeeper-part-time-roofstock-oceanside-oregon-jf6yfgy5zcre) — Oceanside Oregon, United States - [Maintenance Technician](https://feeny.ai/job/maintenance-technician-roofstock-greenville-south-carolina-syd1znahh8h2) — Greenville South Carolina, United States - [Property Inspector](https://feeny.ai/job/property-inspector-roofstock-folly-beach-south-carolina-ap8t5qpwt4d1) — Folly Beach South Carolina, United States - [Recruiter, Operations](https://feeny.ai/job/recruiter-operations-roofstock-dallas-texas-qqcyvdvhdnpf) — Dallas Texas, United States