Senior Maintenance Leader: Field & Office Ops

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

Benefits offered by this job

Vacation time (2 weeks)

Sick time (1 week)

Health insurance (partial)”},{

Job summary

Del Mar Vacations, Inc is seeking a Senior Manager, Maintenance Operations to lead the in-house Maintenance Team, driving same-day issue resolution for guests and homeowners while focusing on utilization, quality control, and cost efficiency.

The role balances in-office leadership (40%) with field quality control (60%), and requires hands-on coaching, KPI ownership, and effective vendor and tool management to deliver 5-star experiences across Del Mar's properties.

Qualifications

• 3-5 years experience leading a maintenance, facilities, or field service team in 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).
• Experience using AI tools (e.g., Claude) to improve personal work output, and ability to teach, train, and lead technicians similarly.

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 model team culture.
• Provide live troubleshooting support to prevent callbacks and escalations.
• Oversee fleet readiness, parts, tools, and information for a successful first visit.
• Review and approve AI-flagged or escalated maintenance jobs; prioritize billable work.

Skills

Leadership

Team coaching

Problem solving

Scheduling

Communication

Tools

Zuper

GPS routing software

Remote lock systems

StayFi

AI tools

Job description

Del Mar Vacations, Inc is seeking a Senior Manager, Maintenance Operations to lead the in-house Maintenance Team, driving same-day issue resolution for guests and homeowners while focusing on utilization, quality control, and cost efficiency.

The role balances in-office leadership (40%) with field quality control (60%), and requires hands-on coaching, KPI ownership, and effective vendor and tool management to deliver 5-star experiences across Del Mar's properties.