Short-term Rental Home Inspector (1099) at Roofstock (Rockaway Beach Oregon, United States)

Roofstock· Rockaway Beach Oregon, United States·6d ago

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.

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Why work at Roofstock

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.

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).

Sources

Job description

Overview

Why work at Roofstock

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