Lead Piecework Housekeeper

First Chair Destinations; Gloucester (MA); On-site; USD 50,000 - 70,000; Full time

Benefits offered by this job

Health Insurance

Dental & Vision Insurance

401(k) with Company Match

Paid Time Off (PTO) & Holidays

Paid Sick Leave

Job summary

First Chair Destinations is seeking a Lead PW Housekeeper to lead housekeeping teams, schedule staff, and maintain high standards of cleanliness across properties. The role includes coaching, inspections, and hands-on cleaning as needed to ensure guest satisfaction.

Ideal candidates bring supervisory experience, tech-savviness with mobile apps, and a collaborative approach to improve efficiency while aligning with company policies.

Qualifications

• Experience working in hotel, hospitality, vacation or similar industry is highly preferred.

Responsibilities

• Oversee daily operations and workflow management to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.

Skills

Supervisory experience

Tech-savvy

Team collaboration

Communication skills

Dependable & self-motivated

Flexible schedule

Customer service

Independent work

Tools

Mobile apps

Tablets

Job description

We offer exceptional vacation homes across the country’s most celebrated ski towns and coastal retreats. Each property is carefully selected, locally managed, and held to an uncompromising standard of care. We live and work in the communities we serve, which means every stay comes with generous local knowledge, genuine hospitality, and the confidence that what you booked is exactly what you’ll find.

We’re proud to offer a competitive benefits package designed to support our employees both at work and beyond. Benefits and eligibility may vary by position and are subject to change. Full plan details and terms will be provided during onboarding.

• Health, Dental & Vision Insurance
• 401(k) with Company Match
• Paid Time Off (PTO)& Holidays (non-exempt employees)
• Paid Flexible Time Off & Holidays (exempt employees only)
• Paid Sick Leave

Benefits are subject to the terms and conditions of the applicable plan documents, which govern in the event of any discrepancy. The Company reserves the right to modify, suspend, or terminate benefit plans and programs at any time.

About This Job

The Lead PW Housekeeper assists the department managers in leading and developing a team of housekeepers through coaching, performance management, and optimizing daily operations to meet productivity and quality standards. You'll assist with scheduling, and fostering a collaborative work environment while participating in hands‑on cleaning and inspections to maintain our high standards.

Compensation + Schedule

• $39 minimum to $350 maximum per clean. Compensation for time picking up supplies, as well as drive time to and from piece rate assignments, are included in the applicable piece rate.
• You will be paid $24 - $25 per hour less payroll deductions and all required withholdings for training, required meetings, non-post reservation cleans, and paid time off.
• 30 - 40 hours per week
• Schedule: 5 days a week, including weekends, fewer hours in the winter months
• Weekends and holidays may be required

Essential Job Functions

• Oversee daily operations and workflow management to optimize team productivity and meet departmental objectives. Identify areas for improvement, and implement process enhancements to drive efficiency and quality outcomes.
• Perform inspections of cleans completed by Housekeepers and support touch‑up cleans as needed.
• Assist managers with supervision of an efficient and high‑quality team of housekeeping personnel ensuring all are trained, effective, and adhere to company policies and procedures.
• Foster a collaborative work environment that promotes open communication, innovation, and employee engagement. Address team conflicts constructively and in a timely manner as they arise.
• Professionally clean and maintain properties using cleaning procedures and products in conformance with prescribed company standards.
• Sweeping, vacuuming, mopping, dusting, and washing all surfaces. move all reasonably portable furniture in rooms to clean under and behind and assist with laundry as needed.
• Assist with scheduling, distribution of tickets, ordering and organizing supplies, as assigned by the manager.
• Meet and maintain company standards and metrics such as NPS, standard unit appearance, and efficiency.
• Assist managers with assigned budget for your portfolio adhering to set annual costs, with the ability to perform a cost‑benefit analysis.
• Support your team with escalated guest and homeowner concerns by responding to emails, calls, and tickets.
• Partner and assist your Business Development Representative when new units join the portfolio.
• Conduct regular inspections prior to guest and owner arrivals.
• Establish and maintain open, collaborative relationships with fellow regional team members and upper management team.
• Provide cross‑coverage for your manager and Co‑Lead(s) when necessary.
• Other duties as assigned because every day is different in hospitality!

Skills + Qualifications

• Experience working in hotel, hospitality, vacation or similar industry is highly preferred.
• 1 - 2 years experience in housekeeping or similar position.
• Prior experience in supervisory or management level position in a similar industry.
• Tech‑savvy with experience using various digital systems and applications and comfortable using mobile apps, tablets, and various software platforms.
• This role involves frequent travel between worksites, so reliable personal transportation is essential.
• Dependable and prepared. Showing up on time and ready to go is key to creating great stays for our guests and peace of mind for our homeowners.
• Must be dependable, self‑motivated, and able to work independently while contributing positively to a collaborative team environment.
• Comfortable talking to people—online or in person—and being able to share information in a way that’s clear, thoughtful, and represents the company in a positive way always.

Workplace Environment + Physical Requirements

• Work may take place indoors or outdoors, in a variety of settings including private homes, resorts, offices, and laundry facilities — often in varying weather conditions.
• We’re in hospitality and our schedules can change based on guest and homeowner needs. Shifts may include early mornings, evenings, weekends, and holidays. We require flexibility to support this.
• Reliable transportation required.
• Regular travel within the locally assigned market and / or region.
• Ability to move freely (balancing, climbing, crawling, driving, squatting, standing, stooping, walking, bending, pushing, pulling, reaching, and repetitive hand/finger motions) and lift up to a maximum of fifty (50) pounds without assistance.

This job description does not identify every requirement of the position. First Chair may change position requirements, responsibilities, and work environment at any time with or without notice.

Some positions may require that you drive a personal vehicle and/or company vehicle for work purposes. Employees who are required to drive a personal vehicle must have reliable transportation, a valid driver’s license, and be at least 18 years of age. Employees who are required to drive a company vehicle must have a valid driver’s license, be at least 21 years of age, and have been a licensed driver for no less than 3 years.

An offer of employment for this role will be contingent upon the successful completion of a background check.

PRIVACY NOTICE: The information you provide through this application will be used solely to evaluate your candidacy for employment with First Chair Destinations. Your information will be kept confidential and accessible only to authorized members of our hiring team and trusted service providers supporting our recruitment process. By submitting your application, you acknowledge that your information will be collected, stored, and processed in accordance with First Chair Destinations' privacy policy and applicable federal, state, and local laws. First Chair Destinations is an Equal Opportunity Employer and does not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, or any other status protected by applicable law. First Chair Destinations participates in E-Verify. If you have questions about how your information is handled, please contact us at [e-mail].

We use Greenhouse’s AI-powered Talent Matching tool to compare your application against our job requirements.