Maintenance Operations Lead for 5-Star Service

Del Mar Vacations; Orleans (MA); On-site; USD 75,000 - 100,000; Full time

Benefits offered by this job

2 weeks vacation

1 week sick time

Health insurance (partial subsidy)

HSA

401k match (up to 4%)

Yearly bonus program

Job summary

Del Mar Vacations in Orleans, MA is seeking a Senior Manager / Maintenance Operations to lead the Maintenance Team and solve issues same-day for guests and homeowners, balancing in-office leadership (40%) and field problem-solving (60%).

This role focuses on utilization, callbacks, quality control, and escalations, acting as the technical expert and motivator to deliver 5-star service while driving profitability.

Qualifications

• 3-5 years experience leading a maintenance, facilities, or field service team; residential, hospitality, or property management settings preferred.
• Strong hands-on technical background; ability to train, coach, and evaluate technician work quality.
• Track record of improving technician utilization through better scheduling, training, and systems.
• Comfortable owning KPIs and communicating performance trends to leadership.
• Experience with field service or maintenance management software (e.g., Zuper or similar platforms).
• Experience using AI tools (e.g., Claude) to improve personal work output, and ability to teach, train, and lead technicians in doing the same.
• A calm, solutions-first leadership style; strong communicator who can move between field, office, and executive leadership

Responsibilities

• Drive day-to-day execution, quality, and profitability of the Maintenance Team; solve problems in the field and lead technicians to deliver 5-star results.
• Be present in-office daily to support recruiting, coach technicians, approve fieldwork, and manage the maintenance schedule and payroll hours.
• Provide live troubleshooting support to technicians to prevent callbacks and escalations.
• Champion use of AI tools to enable technicians to self-serve home information while on-site.
• Oversee fleet readiness, truck inventory, inspections, and permits to keep technicians road-ready.
• Visit service requests and projects in the field to ensure quality, validate completion, and meet homeowner standards.
• Deliver real-time feedback to technicians and translate field observations into retraining or process changes.
• Inspect vendor work prior to invoicing to ensure Del Mar's standards are met.
• Own adoption of tools like Zuper, GPS/routing, remote locks, StayFi, and AI tools; drive performance improvements.
• Review technician performance and schedules; train operations admins on matching the right technician to the right job.
• Partner with warehouse and purchasing leads to ensure parts and information are available for a successful first visit.

Skills

Team leadership

Maintenance management

Scheduling optimization

KPIs ownership

AI tools adoption

Field service

Training & coaching

Technical problem solving

Tools

Zuper

GPS routing software

Remote lock systems

StayFi

AI tools (Claude)

Job description

Del Mar Vacations in Orleans, MA is seeking a Senior Manager / Maintenance Operations to lead the Maintenance Team and solve issues same-day for guests and homeowners, balancing in-office leadership (40%) and field problem-solving (60%).

This role focuses on utilization, callbacks, quality control, and escalations, acting as the technical expert and motivator to deliver 5-star service while driving profitability.