Regional Maintenance Manager

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:

The Regional Maintenance Manager, reporting directly to the Director of Hotel Operations, is responsible for leading facilities and engineering operations across a portfolio of 10 hotel properties in the Northeast.

This role ensures properties are maintained to brand, safety, regulatory, and long-term asset preservation standards. The Regional Maintenance Manager drives preventative maintenance execution, compliance readiness, systems adoption, and leadership accountability across the portfolio.

This position is approximately 50% field-based and 50% administrative, with around 60% travel required.

Organizational Structure:

Area Maintenance Managers own day-to-day property maintenance operations whereas the Regional Maintenance Manager owns standards, oversight, accountability, and portfolio-wide consistency.

What This Role Is NOT

To ensure clarity of expectations, this role is not responsible for:

• Acting as the renovation Project Manager
• Providing daily on-site maintenance coverage at properties
• Supervising construction projects beyond advisory input
• Serving as a long-term on-site Chief Engineer
• Back filling routine labor gaps except during short-term emergencies

This is a leadership and asset preservation role, not a floating technician position.

Essential Duties and Responsibilities

The essential responsibilities include, but are not limited to the following:

Preventative Maintenance & Asset Execution

• Drive 95%+ preventative maintenance completion across the portfolio
• Standardize checklists and PM protocols
• Conduct monthly or bi-monthly property audits
• Identify early signs of asset failure and implement corrective action plans
• Track portfolio-level PM performance and emergency trends

Area Maintenance Manager Leadership

• Lead and support Area Maintenance Managers across all properties
• Conduct weekly L10 cadence calls
• Provide coaching, training, and performance accountability
• Establish consistent standards and execution expectations
• Provide short-term coverage support during absences when necessary

Property Condition Oversight

• Conduct monthly or bi-monthly property walks
• Implement asset condition scoring and documentation
• Identify capital planning needs early
• Ensure post-renovation standards are maintained

Emergency Reduction & Risk Mitigation

• Reduce surprise system failures across the portfolio
• Analyze recurring issues and implement preventative strategies
• Strengthen inspection readiness year-round

Compliance & Regulatory Oversight

• Maintain relationships with DOH, building inspectors, fire officials, and other authorities
• Ensure all properties meet OSHA, pool, health, and safety regulations
• Lead inspection preparation and corrective action processes
• Maintain contractor COIs and compliance documentation

Vendor & Contract Management

• Negotiate and manage vendor contracts (including snow removal and specialty services)
• Standardize preferred vendor relationships
• Recommend cost-saving and efficiency improvements

Systems & Technology Ownership

• Lead full adoption of maintenance software across all properties
• Train Area Maintenance Managers and maintenance teams on proper system usage
• Enforce consistent logging, reporting, and documentation standards
• Audit system accuracy and hold teams accountable
• Utilize system data to identify risk, trends, and operational gaps

Seasonal & Operational Readiness

• Oversee winterization and freeze prevention plans
• Ensure reopening checklists are executed
• Lead pool readiness and seasonal compliance preparation
• Standardize seasonal readiness protocols across properties

Success Measures

• Preventative Maintenance Excellence: 95%+ PM completion rate portfolio-wide with measurable reduction in emergency repairs.
• Inspection Readiness:
  All properties pass OSHA, DOH, and building inspections with no major violations.
• Emergency Reduction:
  Year-over-year decrease in unexpected asset failures.
• Leadership Accountability:
  Area Maintenance Managers consistently executing standardized SOPs and…