Weekender
About The Company
We are a young, fast-growing company (just recognized in the INC 5000 Fastest Growing Companies) of ambitious, mission-driven Weekenders working together to inspire personal growth through adventure, travel and exploration! We specialize in creating inspiring hotel stays for our guests in iconic destinations.
This is a rare opportunity to be paid to learn, have an immediate and lasting impact in a young startup company and culture, and grow personally and professionally with an amazing team.
You will love it at Weekender if our core values below get you excited and inspired too!
Always be a student and always be open-minded
Be Adventurous
Be excited by challenge and willing to fail-forward
Commit to being world class at your job and lean-in to your superpowers
Be a Host
Treat guests and teammates like you would family
Be of Integrity
Own your Domain: Be accountable to your job & the greater mission
Embrace honesty, transparency and vulnerability
Follow-through and do what you say you’re going to do
What you’ll be responsible for: This is a critical, dual-responsibility role acting as the Property Maintenance Manager for our Killington, VT property while also serving as the Area Maintenance Manager for our Peterborough, NH and Manchester, VT properties. This position is responsible for the upkeep and preventative maintenance of rooms, public areas, and major systems, while also overseeing capital and renovation projects across all three locations. The role is both hands‑on and strategic, ensuring safety, cost‑efficiency, and long‑term asset preservation across the portfolio. This position is onsite at our Killington, VT property with required travel to other properties in the region.
Essential Duties and Responsibilities The essential functions include, but are not limited to the following:
Preventative Maintenance Planning
Build and maintain a detailed preventative maintenance calendar for all properties, including new acquisitions
Assign priorities, schedule tasks, and track completion
Train property operators and staff on the impact of preventative maintenance on budget and guest experienceComplete as many preventative tasks in‑house as possible to control expenses
Build and maintain strong relationships with local and regional vendors
Order supplies and equipment at the best available rates
Schedule and oversee third‑party vendors for services beyond in‑house scope, ensuring competitive pricing and quality
Preventative and Routine Tasks May Include:
Boiler system checks
Fireplace maintenance
Structural inspections and basic repairs
Project Management
Maintain an ongoing calendar of large‑scale maintenance projects
Complete feasible projects in‑house to save costs
Plan, source, and negotiate contracts for outsourced services (e.g. snow removal, landscaping)
Act as project manager for capital renovations and upgrades, including budget forecasting, vendor coordination, and stakeholder communication
Facilities & Equipment Management
Diagnose, maintain, and repair building systems, mechanical equipment, and property infrastructure
Manage a running list of maintenance requests, projects, and urgent repairs
Ensure timely, safe, and budget‑conscious task execution
Compliance & Inspections
Attend regulatory inspections and support compliance with DOH, DEC, APA, and other relevant authorities
Maintain documentation and ensure that all vendor paperwork (insurance, W‑9s, etc.) is submitted and up to date before work begins
Support for GMs & Capital Planning
Collaborate with each property’s General Manager to draft yearly maintenance plans and capital “wish lists”
Help ensure execution and follow‑through on those initiatives
Other Duties
Complete assigned work‑related tasks as needed
Participate in relevant management and safety training
Success Measures
Preventative maintenance schedules are completed on time and within budget.
Maintenance‑related guest issues are minimized through proactive upkeep.
Projects and repairs are completed safely, efficiently, and cost‑effectively.
Properties remain compliant with all regulatory and safety standards.
Strong collaboration and communication with General Managers and vendors.
Qualifications
Solid understanding of plumbing, electrical, HVAC, and general building systems
Competency in carpentry, painting, and general maintenance tasks
Skilled at diagnosing and solving maintenance issues efficiently
Excellent interpersonal and communication skills
Physically capable of working in varied conditions, including heat and cold
Able to use hand and power tools safely and effectively
High school diploma or equivalent
Ability to lift or carry up to 50 lbs and be on foot for most of the workday
Ability to bend, crawl, push, pull, and work in physically demanding positions for extended periods
Weekender provides excellent benefits to our salaried employees
Comprehensive Health insurance: 60% employer paid for employee only plans*
Comprehensive Dental & Vision insurance: 100% employer paid for employee only plans*
Life insurance policy: $25k fully paid policy by Weekender
Gym membership reimbursement with health plan (up to $300/ benefit year)
Employee Assistance Program
Competitive 401k Matching Plan with employer match up to 4% of total salary - (eligible after 1000 hours worked)
Discounted employee hotel stays at Weekender properties
3 weeks (15 business days) PTO (vacation/sick) paid vacation per year
Partnership with eCornell for continuous learning in our industry
Low cost Hertz rental cars
Employee referral program
* Subject to change annually based on health, dental and vision plan chosen for the year
The pay range for this role is: 60,000 - 75,000 USD per year (Killington, VT)
#J-18808-Ljbffr
This is a rare opportunity to be paid to learn, have an immediate and lasting impact in a young startup company and culture, and grow personally and professionally with an amazing team.
You will love it at Weekender if our core values below get you excited and inspired too!
Always be a student and always be open-minded
Be Adventurous
Be excited by challenge and willing to fail-forward
Commit to being world class at your job and lean-in to your superpowers
Be a Host
Treat guests and teammates like you would family
Be of Integrity
Own your Domain: Be accountable to your job & the greater mission
Embrace honesty, transparency and vulnerability
Follow-through and do what you say you’re going to do
What you’ll be responsible for: This is a critical, dual-responsibility role acting as the Property Maintenance Manager for our Killington, VT property while also serving as the Area Maintenance Manager for our Peterborough, NH and Manchester, VT properties. This position is responsible for the upkeep and preventative maintenance of rooms, public areas, and major systems, while also overseeing capital and renovation projects across all three locations. The role is both hands‑on and strategic, ensuring safety, cost‑efficiency, and long‑term asset preservation across the portfolio. This position is onsite at our Killington, VT property with required travel to other properties in the region.
Essential Duties and Responsibilities The essential functions include, but are not limited to the following:
Preventative Maintenance Planning
Build and maintain a detailed preventative maintenance calendar for all properties, including new acquisitions
Assign priorities, schedule tasks, and track completion
Train property operators and staff on the impact of preventative maintenance on budget and guest experienceComplete as many preventative tasks in‑house as possible to control expenses
Build and maintain strong relationships with local and regional vendors
Order supplies and equipment at the best available rates
Schedule and oversee third‑party vendors for services beyond in‑house scope, ensuring competitive pricing and quality
Preventative and Routine Tasks May Include:
Boiler system checks
Fireplace maintenance
Structural inspections and basic repairs
Project Management
Maintain an ongoing calendar of large‑scale maintenance projects
Complete feasible projects in‑house to save costs
Plan, source, and negotiate contracts for outsourced services (e.g. snow removal, landscaping)
Act as project manager for capital renovations and upgrades, including budget forecasting, vendor coordination, and stakeholder communication
Facilities & Equipment Management
Diagnose, maintain, and repair building systems, mechanical equipment, and property infrastructure
Manage a running list of maintenance requests, projects, and urgent repairs
Ensure timely, safe, and budget‑conscious task execution
Compliance & Inspections
Attend regulatory inspections and support compliance with DOH, DEC, APA, and other relevant authorities
Maintain documentation and ensure that all vendor paperwork (insurance, W‑9s, etc.) is submitted and up to date before work begins
Support for GMs & Capital Planning
Collaborate with each property’s General Manager to draft yearly maintenance plans and capital “wish lists”
Help ensure execution and follow‑through on those initiatives
Other Duties
Complete assigned work‑related tasks as needed
Participate in relevant management and safety training
Success Measures
Preventative maintenance schedules are completed on time and within budget.
Maintenance‑related guest issues are minimized through proactive upkeep.
Projects and repairs are completed safely, efficiently, and cost‑effectively.
Properties remain compliant with all regulatory and safety standards.
Strong collaboration and communication with General Managers and vendors.
Qualifications
Solid understanding of plumbing, electrical, HVAC, and general building systems
Competency in carpentry, painting, and general maintenance tasks
Skilled at diagnosing and solving maintenance issues efficiently
Excellent interpersonal and communication skills
Physically capable of working in varied conditions, including heat and cold
Able to use hand and power tools safely and effectively
High school diploma or equivalent
Ability to lift or carry up to 50 lbs and be on foot for most of the workday
Ability to bend, crawl, push, pull, and work in physically demanding positions for extended periods
Weekender provides excellent benefits to our salaried employees
Comprehensive Health insurance: 60% employer paid for employee only plans*
Comprehensive Dental & Vision insurance: 100% employer paid for employee only plans*
Life insurance policy: $25k fully paid policy by Weekender
Gym membership reimbursement with health plan (up to $300/ benefit year)
Employee Assistance Program
Competitive 401k Matching Plan with employer match up to 4% of total salary - (eligible after 1000 hours worked)
Discounted employee hotel stays at Weekender properties
3 weeks (15 business days) PTO (vacation/sick) paid vacation per year
Partnership with eCornell for continuous learning in our industry
Low cost Hertz rental cars
Employee referral program
* Subject to change annually based on health, dental and vision plan chosen for the year
The pay range for this role is: 60,000 - 75,000 USD per year (Killington, VT)
#J-18808-Ljbffr