Diamond Landscaping · 1 day ago
Fleet Director
Los Angeles, CA
Full-time
Onsite
Director/Executive
$120K/yr - $160K/yr
7+ years expDiamond Landscaping has been a trusted partner to high-net-worth residential clients for over 30 years, and they are seeking a Director of Fleet Operations to evolve their fleet strategy. This role involves overseeing fleet performance, ensuring safety and compliance, and implementing digital systems to enhance operations across multiple companies.
Environmental Services
Responsibilities
Own and continuously evolve Diamond’s platformwide fleet strategy, policies, and governance
Establish scalable standards for vehicles, equipment, maintenance, and compliance that support growth and acquisitions
Lead fleet integration for new operating companies, including asset assessment, digital system onboarding, and risk alignment
Serve as the internal authority on fleet-related risk, cost, safety, and operational trade-offs
Champion a safety-first mindset across the fleet organization; safety is not a priority that shifts; it is a non-negotiable operating expectation
Partner closely with Diamond’s Safety, Operations, and Field Leadership teams to proactively mitigate risk and prevent accidents before they occur
Lead the implementation and continuous improvement of driver safety programs, including training, coaching, and accountability standards
Use telematics, cameras, and incident data to identify unsafe behaviors, trends, and leading indicators, then translate insights into corrective action
Ensure thorough investigation, documentation, and rootcause analysis of all vehicle incidents, with a focus on corrective action plans to reduce risk and liability, including prevention and learning, not blame
Ensure full compliance with all city, state, and federal environmental and emissions regulations, including DOT and California-specific requirements, while preparing the platform to scale into other highly regulated markets
Develop and maintain fleet policies and procedures to ensure consistent compliance across all operating divisions
Monitor and interpret evolving regulatory requirements and proactively adapt fleet operations to ensure continued compliance
Own vehicle registration, inspections, licensing, insurance documentation, and renewal processes across the platform
Maintain audit-ready records for all fleet assets, drivers, incidents, and compliance activities
Lead Diamond’s transition to a fully digitized fleet operation, replacing manual, paper-based processes with integrated systems
Serve as the executive owner and champion for the selection, implementation, and ongoing optimization of fleet technology platforms as the business scales, including: telematics and GPS systems (future state selection and rollout), vehicle and driver camera solutions (future state selection and rollout), digital maintenance, inspection, and workorder management, asset tracking and utilization reporting, licensing, registration, and insurance management systems
Lead change management to ensure tools are adopted in a field-friendly, frictionless way that improves safety, efficiency, and compliance—not bureaucracy
Leverage data to drive decisions on utilization, replacement timing, safety performance, fuel efficiency, and total cost of ownership
Lead the selection, implementation, and ongoing optimization of a platform-wide fuel card program
Establish fuel policies, controls, and reporting to prevent misuse, reduce fraud, and improve accountability
Analyze fuel consumption trends by vehicle, crew, and geography to identify costreduction and efficiency opportunities
Partner with Operations and Finance to align fuel strategy with routing, utilization, equipment selection, and behavior-based safety initiatives
Lead preventative maintenance, inspection, and repair programs to maximize vehicle uptime and asset life
Determine when in-house repairs are appropriate versus third-party vendors; manage vendor performance and cost discipline
Develop and execute initiatives to reduce fuel spend, accident frequency, repair costs, and overall fleet cost per vehicle
Own the strategic relationship with Diamond’s fleet management partner, serving as the primary point of accountability and escalation
Lead partner selection, contract negotiation, performance management, and continuous optimization to ensure service levels, cost discipline, and scalability
Forecast fleet needs and lead procurement, disposal, and replacement planning for vehicles, trailers, and equipment
Partner with Finance on purchasing processes, financing strategies, capital planning, and annual budgets
Ensure continuous insurance coverage for all vehicles and authorized drivers; manage policy updates, claims coordination, and risk exposure
Provide clear, data-driven fleet reporting to executive leadership
Leverage telematics and fleet data to track performance metrics, identify trends, and drive continuous improvement in up-time and cost efficiency
Build trust and credibility with branch leaders, supervisors, and crews through practical support and field presence
Communicate proactively regarding vehicle availability, downtime, and maintenance schedules
Train and reinforce driver standards related to safety, compliance, and responsible vehicle use
Model accountability, craftsmanship, and continuous improvement
Qualification
Required
Bachelor's degree in Business, Operations, Logistics, Finance, or a related field, or equivalent practical experience, will be considered
7+ years of progressive fleet or operations leadership experience in landscaping, construction, or field service environments
Strong working knowledge of trucks, trailers, and equipment, including hands-on mechanical experience for diagnostics and minor repairs
Proven experience operating in highly regulated environments, including DOT compliance
Demonstrated success in implementing digital fleet, telematics, and asset management platforms
Experience with vendor management, contract negotiation, invoicing, and cost analysis
Ability to balance strategic thinking with hands-on execution
Strong communicator who can work effectively with field teams and executives
Valid driver's license and clean driving record
High integrity, sound judgment, and a strong sense of ownership
Preferred
Spanish-speaking capability is a strong plus, given the nature of our field-based workforce
Benefits
Comprehensive benefits package
Paid time off
Long-term growth opportunity within a scaling, private equity-backed platform
Company
Diamond Landscaping
For over 30 years, Diamond Landscaping has been a trusted partner to discerning homeowners across the Los Angeles area, delivering exceptional landscapes through thoughtful design, precise installation, and disciplined long-term care.
501-1000 employees
Funding
Current Stage
Late StageCompany data provided by crunchbase