Contract Maintenance Manager, Arizona

About the company

The company exists to enrich lives by making second home ownership possible and enjoyable for more people. We've reimagined the second home category — pairing a thoughtfully designed co-ownership model with simplified financials, equitable scheduling, and dedicated local property management, so owners get the joy of a true second home without the hassle.

Since launch, the company has facilitated more than $1.2 billion in gross real estate transactions and service fees across 40+ destinations in the U.S., Mexico, and Europe — including Aspen, Lake Tahoe, Napa, Malibu, Palm Springs, Cabo, Paris, London, and most recently Florence, Milan, and Rome. We've raised over $300 million in cumulative equity funding , closed the largest real estate Regulation A+ offering of 2025, and reserved the Nasdaq ticker PCSO as we build toward a public listing.

Our work has been featured in The New York Times , The Wall Street Journal , Fortune , Forbes , CNBC , Bloomberg , and others.

Recognition

We're a Certified Great Place to Work and have been honored for both our culture and our category-defining work:

• No. 5, Forbes America's Best Startup Employers (2026) — our second consecutive Top 10 ranking

• Newsweek's America's Greatest Startup Workplaces (2025)

• Winner, 2025 Inman Best of Proptech Awards — Consumer Experience & Marketplace Innovation

• Fortune & Great Place To Work Best Workplaces in Real Estate (2024)

• Best Workplace in the Bay Area™ (2023)

• LinkedIn Top Startup (2022) · Glassdoor Best Places to Work, #6 (2022)

Contract Maintenance Manager

Position Type: Independent Contractor (1099)

Compensation: Hourly Rate $45 an hour

Position Overview

The Contract Maintenance Manager is responsible for executing maintenance and repair work across a portfolio of the company luxury homes. Operating as an independent contractor on behalf of the company, this role serves as an extension of our Asset Management team, ensuring homes are maintained to the company's luxury standards and consistently ready for owner stays.

This is a hands-on, hourly contract position focused on delivering high-quality repairs, responding quickly to maintenance needs, and providing a professional, seamless experience for the company owners.

Contract Maintenance Managers represent the company while performing assigned services and are expected to uphold the same standards of quality, professionalism, communication, and attention to detail as the company's internal Maintenance Managers.

Key Responsibilities

Maintenance Execution & Repairs

• Complete assigned maintenance work orders across a portfolio of the company homes.

• Perform general handyman repairs, troubleshooting, and preventative maintenance.

• Diagnose and address common issues involving plumbing, electrical, HVAC basics, appliances, fixtures, and smart home technology.

• Identify repairs requiring specialized or licensed vendors and communicate recommendations to the Asset Management team.

• Complete work efficiently, safely, and correctly the first time, following the company Home Standards.

Work Order Management & Communication

• Coordinate with the company's Operations Manager of Maintenance and Asset Managers on scheduling, priorities, and work assignments.

• Respond promptly to urgent maintenance requests, including issues impacting active owner stays.

• Provide timely updates on repair status, estimated completion times, and any additional work required.

• Document completed work, including labor hours, materials used, photos, and repair details, in the company's work order system or other documentation tools.

• Communicate professionally with owners, vendors, and the company team members while representing the company.

Home Readiness & Quality Standards

• Ensure maintenance work supports a safe, functional, and luxury-level home experience.

• Identify potential maintenance concerns and proactively recommend repairs or preventative measures.

• Maintain a high standard of workmanship, cleanliness, and attention to detail when working inside the company homes.

• Protect home finishes, furnishings, and equipment while performing repairs.

• Support Asset Managers in maintaining consistent property standards across the portfolio.

Hourly Billing & Documentation

• Accurately track and submit hours worked against assigned maintenance work orders.

• Document materials purchased and expenses incurred in accordance with the company's contractor billing procedures.

• Provide complete and timely documentation to support accurate property-level billing.

• Obtain approval before performing work outside the agreed scope or incurring additional expenses, as required.

Qualifications

• 5+ years of experience in residential maintenance, handyman services, or property repairs.

• Strong troubleshooting and repair skills across residential home systems.

• Experience working in luxury residential properties, vacation homes, or high-end property management preferred.

• Ability to work independently, manage assigned work efficiently, and deliver consistent quality.

• Strong attention to detail and pride in workmanship.

• Excellent communication skills and professionalism when interacting with owners and the company team members.

• Comfortable using mobile technology, work order systems, and digital documentation tools.

• Reliable transportation and appropriate tools to perform general maintenance services.

• Ability to provide proof of insurance and any applicable licenses or certifications required for the services performed.

Contractor Engagement Details

• Engagement Type: Independent Contractor (1099); not a full-time the company employee.

• Compensation: Agreed-upon hourly rate for authorized maintenance services.

• Work Availability: Assignments based on property maintenance needs, contractor availability, and agreed service expectations.

• Scheduling: Work coordinated with the company's Operations Manager of Maintenance and Asset Management team.

• Service Standards: Contractors are expected to represent the company professionally and follow applicable home care, safety, communication, and documentation standards.

• Payment: Based on approved hours worked and submitted invoices, in accordance with the contractor agreement.

• Tools & Equipment: Contractors are generally responsible for providing their own standard tools and equipment unless otherwise agreed.

• Employment Benefits: This engagement does not include the company employee benefits, paid time off, or other employee compensation programs.

Why You'll Love Working Here

We invest in our Crew the way we invest in our homes — thoughtfully, generously, and with care.

• Competitive base salary and meaningful equity — every Crew member shares in what we're building

• Discretionary time off — take the rest you need, when you need it

• Premium medical, dental, and vision coverage for you and your family

• Sponsored memberships to One Medical, Peloton, and WellHub for whole-person, modern healthcare

• 401(k) to help you build long-term security

• Paid parental leave for primary and secondary caregivers

• Home office stipend and a monthly internet and cell phone reimbursement to set you up for great remote work

• Quarterly team gatherings and ongoing learning and development investment

Our Commitment

The company is proud to be an equal opportunity employer. We welcome applicants of every race, religion, national origin, gender, sexual orientation, gender identity, gender expression, age, ability, and background — including veterans and individuals with disabilities. We believe a Crew as diverse as the owners we serve makes the company stronger, and we're committed to building a workplace where every voice belongs.