Senior Maintenance Ops Leader - Field-First 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 time

Health insurance subsidy

HSA

401k match

Annual bonus

Job summary

Del Mar Vacations seeks a Senior Manager, Maintenance Operations to lead the day-to-day performance of the Maintenance Team on Cape Cod. You will own issue resolution for guests and homeowners, balancing field problem solving with office leadership to deliver 5-star experiences.

You will split time: about 60% in the field and 40% in-office, driving quality, scheduling, and profitability. Strong technical and people skills are required, plus comfort with AI tools.

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 fluidly between the field and the office, and between technicians and executive leadership

Responsibilities

• Drive the day-to-day execution, quality, and profitability of Del Mar's Maintenance Team; solving problems in the field and leading technicians to consistently deliver 5-star results.
• Be present and available in-office daily to support recruiting, coach technicians in real time, approve fieldwork, build the maintenance team schedule, approve weekly payroll hours, and model the standard for team culture.
• Provide live troubleshooting support — answer calls and jump in to help technicians problem-solve from the field, preventing callbacks and avoidable escalations.
• Champion the use of AI tools (including Claude) as a resource for technicians, enabling them to self-serve home information and troubleshooting support while on-site.
• Support recruiting and onboarding for new technicians, ensuring alignment to Del Mar's 5-star standard from day one.
• Oversee fleet readiness — truck inventory, inspections, and permits — to keep every technician road-ready.
• Visit service requests, jobs, and projects in the field to solve problems same-day, inspect quality, validate completion, and confirm work meets homeowner standards.
• Deliver direct, real-time feedback to technicians based on field observations — reinforcing wins and correcting misses.
• Identify trends and repeat issues and translate them into team retraining or process improvements.
• Inspect vendor-completed jobs and projects prior to invoicing to confirm they meet Del Mar's standards.
• Serve as the team's technology lead, owning adoption and use of tools including Zuper, GPS/routing software, remote lock systems, StayFi, and AI tools.
• Drive performance improvements with a goal of reducing callbacks by 50%.
• Review technician performance and schedules, training operations admins on matching the right technician to the right job.
• Partner with warehouse and purchasing leads to ensure every technician has the parts, tools, and information needed for a successful first visit, every time.

Skills

Maintenance leadership

Field service

Quality control

Coaching

AI tools

Scheduling

Tools

Zuper

GPS routing

StayFi

Claude

Job description

Del Mar Vacations seeks a Senior Manager, Maintenance Operations to lead the day-to-day performance of the Maintenance Team on Cape Cod. You will own issue resolution for guests and homeowners, balancing field problem solving with office leadership to deliver 5-star experiences.

You will split time: about 60% in the field and 40% in-office, driving quality, scheduling, and profitability. Strong technical and people skills are required, plus comfort with AI tools.