Senior Maintenance Ops Leader — 5-Star Service

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

Benefits offered by this job

2 weeks vacation

1 week sick leave

Health insurance

HSA

401k with up to 4% match

Yearly bonus program

Job summary

Del Mar Vacations in Orleans, MA, seeks a Senior Manager of Maintenance Operations to lead daily performance of the Maintenance Team, solving issues the same day for guests and homeowners. The role blends in-office leadership (40%) with field quality work (60%), driving 5-star experiences with a focus on utilization, quality control, and escalations.

The ideal candidate will manage scheduling, training, and vendor coordination while championing AI tools to optimize field workflows and

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.

Responsibilities

• Drive the day-to-day execution, quality, and profitability of the Maintenance Team; solving problems in the field and leading technicians to deliver 5-star results.
• Be present in-office daily to support recruiting, coach technicians, approve fieldwork, build the schedule, approve payroll hours, and model team culture.
• Provide live troubleshooting support to technicians, preventing callbacks and escalations.
• Oversee fleet readiness — truck inventory, inspections, and permits.
• Visit service requests, inspect quality, validate completion, and confirm homeowner standards.
• Lead adoption of AI tools as a resource for technicians on-site.

Skills

Leadership

Maintenance operations

Field service

AI tools (Claude)

Team coaching

Tools

Zuper

Claude

GPS routing

Job description

Del Mar Vacations in Orleans, MA, seeks a Senior Manager of Maintenance Operations to lead daily performance of the Maintenance Team, solving issues the same day for guests and homeowners. The role blends in-office leadership (40%) with field quality work (60%), driving 5-star experiences with a focus on utilization, quality control, and escalations.

The ideal candidate will manage scheduling, training, and vendor coordination while championing AI tools to optimize field workflows and