Senior Manger, Maintenance Operations

Del Mar Vacations; Orleans (MA); On-site; USD 110,000 - 170,000; Full time

Job summary

Del Mar Vacations in Orleans, MA seeks a Senior Manager, Maintenance Operations to lead our Maintenance Team, driving day-to-day performance, problem solving, and 5-star guest and homeowner experiences. The role blends in-office leadership (40%) with in-field quality control and problem solving (60%).

You will coach technicians, optimize scheduling and utilization, oversee fleet readiness, coordinate with vendors, and champion AI tools to boost efficiency while delivering consistent,

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, & evaluate technician work quality.
• Track record of improving technician utilization through better scheduling, training, & systems.
• Experience with field service or maintenance management software (e.g., Zuper or similar platforms).
• Experience using AI tools (Claude) to improve personal work output, & ability to teach, train, & lead technicians in doing the same.

Responsibilities

• Drive the day-to-day execution, quality, & profitability of Del Mar's Maintenance Team; solving problems in the field & leading technicians to consistently deliver 5-star results.
• Be present & available in-office daily to support recruiting, coach technicians in real time, approve fieldwork, build the maintenance team schedule, approve weekly payroll hours, & model the standard for team culture.
• Provide live troubleshooting support - answer calls & jump in to help technicians problem-solve from the field, preventing callbacks & avoidable escalations.
• Champion the use of AI tools as a resource for technicians, enabling them to self-serve home information & troubleshooting support while on-site.
• Oversee fleet readiness - truck inventory, inspections, & permits - to keep every technician road-ready.
• Review & approve all AI-flagged or escalated maintenance jobs daily, prioritizing billable work first.

Skills

Maintenance leadership

Field service management

Team coaching

KPIs & analytics

Technical troubleshooting

AI tools

Vendor management

Tools

Zuper

GPS/routing software

Remote lock systems

StayFi

Claude (AI tools)

Job description

The Senior Manager, Maintenance Operations leads the day-to-day performance of Del Mar's Maintenance Team. This individual owns the team's ability to solve issues the same day for guests & homeowners - creatively, resourcefully, & without over-relying on outside vendors. With a sharp focus on utilization, callbacks, quality control, & escalations, this role is the connective tissue between scheduling, quality control, team development, & field efficiency. You'll serve as the go-to technical expert, quality enforcer, & team motivator, delivering 5-star guest & owner experiences profitably. This role splits time between in-office leadership (about 40%) & in-the-field quality control & problem-solving (about 60%).

Core Responsibilities

Drive the day-to-day execution, quality, & profitability of Del Mar's Maintenance Team; solving problems in the field & leading technicians to consistently deliver 5-star results.

Team Leadership & Culture

Be present & available in-office daily to support recruiting, coach technicians in real time, approve fieldwork, build the maintenance team schedule, approve weekly payroll hours, & model the standard for team culture. Build trust, momentum, & accountability across the Maintenance Team; set the tone, expectations, & morale for the group. Provide live troubleshooting support - answer calls & jump in to help technicians problem-solve from the field, preventing callbacks & avoidable escalations. Champion the use of AI tools (including Claude) as a resource for technicians, enabling them to self-serve home information & troubleshooting support while on-site. Support recruiting & onboarding for new technicians, ensuring alignment to Del Mar's 5-star standard from day one. Oversee fleet readiness - truck inventory, inspections, & permits - to keep every technician road-ready.

Field Quality Control & Problem Solving

Visit service requests, jobs, & projects in the field to solve problems same-day, inspect quality, validate completion, & confirm work meets homeowner standards. Deliver direct, real-time feedback to technicians based on field observations - reinforcing wins & correcting misses. Identify trends & repeat issues & translate them into team retraining or process improvements. Inspect vendor-completed jobs & projects prior to invoicing (particularly high-value work or unfamiliar vendors) to confirm they meet Del Mar's standards.

Technology & Systems Oversight

Serve as the team's technology lead, owning adoption & use of tools including Zuper, GPS/routing software, remote lock systems, StayFi, & AI tools. Drive performance improvements with a goal of reducing callbacks by 50%. Review technician performance & schedules, training operations admins on matching the right technician to the right job. Partner with warehouse & purchasing leads to ensure every technician has the parts, tools, & information needed for a successful first visit, every time.

Workflow & Billing Oversight

Review & approve all AI-flagged or escalated maintenance jobs daily, prioritizing billable work first. Ensure accuracy of scope, labor, & parts documentation before jobs are handed off to billing. Enforce consistent warehouse & inventory procedures across the technician team.

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, & evaluate technician work quality. Track record of improving technician utilization through better scheduling, training, & systems. Comfortable owning KPIs & 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, & ability to teach, train, & lead technicians in doing the same. See complete job description wh n applying.