Maintenance Operations Lead: 5-Star Field & Team

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

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,