Property & Area Maintenance Manager (Killington)

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!

• Embrace a Growth Mindset
• Always be a student and always be open-minded
• Be Adventurous
• Be excited by challenge and willing to fail-forward
• Be a Ninja
• 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 experience
• Complete as many preventative tasks in-house as possible to control expenses
  
  

Vendor & Supply Management

• 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
  
  

Benefits

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)
• Aflac supplemental benefits
• 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)