Regional Maintenance Manager

About The CompanyWe 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 MindsetAlways be a student and always be open-mindedBe AdventurousBe excited by challenge and willing to fail-forwardBe a NinjaCommit to being world class at your job and lean-in to your superpowersBe a HostTreat guests and teammates like you would familyBe of IntegrityOwn your Domain: Be accountable to your job & the greater missionEmbrace honesty, transparency and vulnerabilityFollow-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 ManagerProviding daily on-site maintenance coverage at propertiesSupervising construction projects beyond advisory inputServing as a long-term on-site Chief EngineerBackfilling 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 portfolioStandardize checklists and PM protocolsConduct monthly or bi-monthly property auditsIdentify early signs of asset failure and implement corrective action plansTrack portfolio-level PM performance and emergency trends

Area Maintenance Manager Leadership

Lead and support Area Maintenance Managers across all propertiesConduct weekly L10 cadence callsProvide coaching, training, and performance accountabilityEstablish consistent standards and execution expectationsProvide short-term coverage support during absences when necessary

Property Condition Oversight

Conduct monthly or bi-monthly property walksImplement asset condition scoring and documentationIdentify capital planning needs earlyEnsure post-renovation standards are maintained

Emergency Reduction & Risk Mitigation

Reduce surprise system failures across the portfolioAnalyze recurring issues and implement preventative strategiesStrengthen inspection readiness year-round

Compliance & Regulatory Oversight

Maintain relationships with DOH, building inspectors, fire officials, and other authoritiesEnsure all properties meet OSHA, pool, health, and safety regulationsLead inspection preparation and corrective action processesMaintain contractor COIs and compliance documentation

Vendor & Contract Management

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

Systems & Technology Ownership

Lead full adoption of maintenance software across all propertiesTrain Area Maintenance Managers and maintenance teams on proper system usageEnforce consistent logging, reporting, and documentation standardsAudit system accuracy and hold teams accountableUtilize system data to identify risk, trends, and operational gaps

Seasonal & Operational Readiness

Oversee winterization and freeze prevention plansEnsure reopening checklists are executedLead pool readiness and seasonal compliance preparationStandardize 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 meeting performance expectations.Systems Enforcement: Maintenance software fully adopted, consistently used, and audit-ready across all properties.Seasonal Preparedness: Properties fully prepared for winter, reopening, and peak seasons without preventable operational disruptions.

Qualifications

5+ years of facilities or maintenance leadership experience (hospitality preferred)Multi-property oversight experience strongly preferredOSHA certification &  pool certification preferredStrong knowledge of HVAC, plumbing, electrical, and life safety systemsExperience leading maintenance managers or senior techniciansProven experience implementing standardized processes and systemsExperience managing vendors and supporting CapEx planningComfortable using reporting dashboards and maintenance softwareWillingness to travel approximately 60%Valid driver’s license and clean driving recordAbility to work in varying temperatures and field environmentsThe pay range for this role is:75,000 - 85,000 USD per year(Saratoga Springs, NY)