Senior Manager / Maintenance Operations

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

Senior Manager / Maintenance Operations

Del Mar Vacations Orleans, Massachusetts, United States

About this position

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 and homeowners — creatively, resourcefully, and without over-relying on outside vendors. With a sharp focus on utilization, callbacks, quality control, and escalations, this role is the connective tissue between scheduling, quality control, team development, and field efficiency. You'll serve as the go-to technical expert, quality enforcer, and team motivator, delivering 5-star guest and owner experiences profitably.

This role splits time between in-office leadership (about 40%) and in-the-field quality control and problem-solving (about 60%).

Core 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.

Team Leadership & Culture

• 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.
• Build trust, momentum, and accountability across the Maintenance Team; set the tone, expectations, and morale for the group.
• 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.

Field Quality Control & Problem Solving

• 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 (particularly high-value work or unfamiliar vendors) 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.

Workflow & Billing Oversight

• Review and approve all AI-flagged or escalated maintenance jobs daily, prioritizing billable work first.
• Ensure accuracy of scope, labor, and parts documentation before jobs are handed off to billing.
• Enforce consistent warehouse and 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, 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

Why Join the Del Mar Vacations Team

Del Mar Vacations is a Veteran‑owned and operated, full‑service vacation rental company on Cape Cod. We specialize in providing 5‑star experiences to our guests, homeowners and each other. As a hospitality and service first culture, our team and their talents are the key to our success.

Working at Del Mar means you will be surrounded by passionate, smart, and engaged people who are focused on superior problem solving and outstanding customer service. Our ideal candidates enjoy working in a small, tight‑knitted, high energy and supportive team, are intellectually curious, comfortable with ambiguity, have a positive outlook, and are able to pivot quickly as things change.

• 2 weeks of vacation time
• 1 week of sick time
• Partially subsidized health insurance
• HSA (health savings account)
• 401k with up to 4% match
• Yearly bonus program (and other rewards and recognition both big and small)

Salary Range

$75,000-$100,000 + bonus

Del Mar Vacation, Inc is an equal opportunity employer. All employment will be decided solely on the basis of your qualifications and merit and according to hiring needs. We are committed to creating a collaborative team and do not to discriminate based off race, color, religion, creed, gender, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender identity or expression, national origin, ancestry, age, disability, genetic information, marital status, amnesty, status as a covered veteran, military service, or any other class protected by applicable federal, state, and local law