Los Angeles
Job Description Director of Fleet Operations Location: Van Nuys, CA Reports to: Chief Financial Officer (CFO) For more than 30 years, Diamond Landscaping has been a trusted partner to high‐net‐worth residential clients, designers, and general contractors—creating exceptional outdoor environments through craftsmanship, precision, and reliability. As we continue to scale our platform through organic growth and acquisitions, we are building the infrastructure, systems, and leadership required to support a best‐in‐class field organization. We are seeking a Director of Fleet Operations to own and evolve our fleet strategy across the Diamond platform. This is a hands‐on, roll‐up‐your‐sleeves leadership role—responsible not only for day‐to‐day fleet performance, but for building scalable, digital‐first systems, ensuring uncompromising safety and compliance, and enabling reliable field operations across multiple operating companies. This role is based in Los Angeles, CA and reports to the Chief Financial Officer, with close day‐to‐day partnership with Operations, Safety, Finance, and Branch Leadership. Role Overview The Director of Fleet Operations is accountable for the end‐to‐end safety, performance, compliance, and cost efficiency of Diamond’s fleet of vehicles, trailers, and related equipment. This leader serves as the platform owner for fleet strategy—standardizing where it creates value, remaining flexible where field conditions demand it, and ensuring Diamond’s crews operate with safe, well‐maintained, and fully compliant assets. A core mandate of this role is to embed a safety‐first, digital‐first operating model—leveraging technology, data, and disciplined processes to prevent incidents, reduce friction for operators, and replace manual paperwork with efficient, auditable systems. Key Responsibilities Fleet Strategy & Platform Leadership • Own and continuously evolve Diamond’s platform‐wide 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., • 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 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., • 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 work‐order 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., • 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 cost‐reduction and efficiency opportunities., • 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., • 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., • 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. What You’ll Bring • Bachelor’s degree in Business, Operations, Logistics, Finance, or a related field—or equivalent practical experience., • 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 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 alike., • Valid driver’s license and clean driving record., • High integrity, sound judgment, and a strong sense of ownership., • Spanish-speaking capability is a strong plus, given the nature of our field-based workforce. Compensation & Benefits We offer a competitive total rewards package, including: • Salary range: $120,000 – $150,000 (final offer dependent on experience, skills, and qualifications), • Comprehensive benefits package, • Paid time off, • Long‐term growth opportunity within a scaling, private‐equity‐backed platform Equal Opportunity Employer Diamond is an Equal Opportunity Employer. We are committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic. Company DescriptionFor 30 years, Diamond Landscaping has been the leader in luxury residential landscaping for high-net-worth clients, including A-list celebrities and media/entertainment executives, in the Los Angeles area. With a focus on custom installation, meticulous craftsmanship, and long-term maintenance, we create dream landscapes and build lifelong relationships.For 30 years, Diamond Landscaping has been the leader in luxury residential landscaping for high-net-worth clients, including A-list celebrities and media/entertainment executives, in the Los Angeles area. With a focus on custom installation, meticulous craftsmanship, and long-term maintenance, we create dream landscapes and build lifelong relationships.