Senior Manager / Maintenance Operations

Del Mar Vacations•Orleans, MA

4d•$75,000 - $100,000•Hybrid

About The Position

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. This role involves being 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. The Senior Manager will build trust, momentum, and accountability across the Maintenance Team, setting the tone, expectations, and morale for the group. They will 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, including truck inventory, inspections, and permits, to keep every technician road-ready. The role also includes visiting 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. 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.

Requirements

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

Nice To Haves

Ability to pivot quickly as things change
Intellectually curious
Comfortable with ambiguity
Positive outlook

Responsibilities

Drive the day-to-day execution, quality, and profitability of Del Mar's Maintenance Team
Solve problems in the field and lead 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
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
Support recruiting and onboarding for new technicians
Oversee fleet readiness — truck inventory, inspections, and permits
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
Identify trends and repeat issues and translate them into team retraining or process improvements
Inspect vendor-completed jobs and projects prior to invoicing
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
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