Chief Estimator

Job Description

Job DescriptionAbout Diamond Landscaping For more than 30 years, Diamond Landscaping has been a leader in luxury residential landscape design, installation, and maintenance throughout the Los Angeles area. We serve discerning homeowners, estates, designers, architects, and industry professionals who expect exceptional craftsmanship, discretion, responsiveness, and enduring quality. Our work is defined by meticulous execution, thoughtful collaboration, and a deep respect for the distinctive character of every property. Position Overview Diamond Landscaping is seeking an experienced Chief Estimator to lead the estimating function (people and process) for high-end residential landscape construction and enhancement projects. This role will oversee the preparation of accurate, detailed, and competitive estimates for complex projects ranging from estate landscapes and outdoor living environments to gardens, pools, hardscape, lighting, irrigation, planting, and specialty installations. The Chief Estimator will partner closely with clients, designers, architects, project managers, operations leaders, vendors, and subcontractors to understand project scope, identify risk, develop sound pricing strategies, and ensure that estimates reflect Diamond’s standards for quality, craftsmanship, and service. The ideal candidate combines strong technical estimating expertise on progressively larger multi-million projects with exceptional judgment, organization, communication, and a genuine appreciation for luxury residential work. Essential Responsibilities

• Lead the full estimating process and management of team from initial opportunity review through proposal submission and handoff to operations.
• Review plans, specifications, drawings, site conditions, design concepts, and client requirements to develop comprehensive project estimates.
• Prepare and review team’s detailed takeoffs for hardscape, planting, irrigation, drainage, lighting, carpentry, masonry, water features, outdoor structures, grading, demolition, and related scopes.
• Build and ensure team has documented accurate labor hours, material, equipment, subcontractor, overhead, contingency, and margin calculations.
• Develop clear, polished, and highly professional proposals appropriate for luxury residential clients and design professionals.
• Conduct site walks and preconstruction reviews to evaluate existing conditions, access, logistics, constructability, scheduling, and help define risk for project team as well as create and review project goals.
• Solicit, evaluate, and negotiate favorable pricing (group pricing/discounts) from vendors, specialty trades, subcontractors, nurseries, material suppliers, and manufacturers.
• Create submittal lists for each project.
• Update and maintain reliable databases of current labor, material, equipment, and subcontractor costs.
• Identify long lead time items, scope gaps, exclusions, assumptions, allowances, alternates, and opportunities for value engineering.
• Collaborate with project management, business leaders, business developer and other estimators to evaluate opportunities and prioritize pursuits aligned with Diamond’s capabilities and standards.
• Participate in client, architect, designer, and internal project review meetings as needed.
• Support the transition from estimating to project management by clearly communicating assumptions, pricing rationale, scope details, and execution considerations.
• Review change orders, submittal requirements, open RFIs, project goals, revised drawings, value-engineering options, and additional work requests for pricing accuracy.
• Assist with estimating strategy, process improvement, historical cost analysis, and estimating systems development.
• Create and maintain standardized templates, procedures, cost libraries, and estimating benchmarks.
• Promote consistency, accountability, and best practices across all estimating activities.
• Protect confidential client, project, pricing, and company information.

Qualifications

• 7 or more years of estimating experience in landscape construction, luxury residential construction, specialty construction, or a closely related field including experience managing estimating teams.
• Demonstrated experience estimating complex, progressively larger and more impactful, high-value residential projects.
• Strong knowledge of landscape construction methods, materials, labor requirements, and sequencing.
• Ability to interpret architectural, landscape, irrigation, lighting, and engineering plans.
• Proven experience with quantity takeoffs, subcontractor solicitation, cost analysis, bid leveling, and proposal preparation.
• Strong understanding of project budgets, gross margin, markups, contingencies, and financial controls.
• Experience with estimating, project management, scheduling, or construction software.
• Advanced proficiency with Microsoft Excel, Aspire, MS Project, Procore, PlanGrid, and related business tools.
• Exceptional attention to detail and accuracy.
• Strong written and verbal communication skills.
• Ability to manage multiple estimates and deadlines in a fast-paced environment.
• Professional presence and confidence working with high-net-worth clients, architects, designers, vendors, and subcontractors.
• Valid California driver’s license and ability to travel to project sites throughout the Los Angeles region.

Preferred Qualifications

• Bachelor’s degree in construction management, landscape architecture, horticulture, engineering, business, or a related field.
• Experience with luxury estate, hospitality, boutique commercial, or highly customized residential construction.
• Familiarity with Southern California plant material, construction practices, permitting considerations, and specialty trades.
• Experience implementing estimating standards, cost databases, or centralized estimating processes.
• Bilingual English/Spanish communication skills are a plus.

Key Attributes - the successful candidate will be:

• Analytical, disciplined, and highly organized
• Commercially astute and financially responsible
• Curious, resourceful, and solutions-oriented
• Comfortable making informed decisions with incomplete information
• Collaborative and respectful of field expertise
• Detail-oriented without losing sight of the larger project vision
• Passionate about craftsmanship and quality
• Discreet, polished, and service-minded
• Committed to honesty, accountability, and continuous improvement

Measure of Success

• Success in this role will be measured by:
• The accuracy and consistency of estimates
• Healthy project margins and reliable cost assumptions
• Timely completion of proposals and bid submissions
• Quality of subcontractor and vendor pricing
• Effective identification and management of project risk
• Smooth transitions from estimating to operations
• Strong relationships with clients, designers, vendors, and internal teams
• Continued improvement of estimating systems, processes, and cost intelligence

Diamond Landscaping offers a competitive compensation package based on experience and qualifications, along with opportunities for professional growth, leadership development, and long-term advancement within a respected luxury landscape organization. Equal Opportunity Diamond Landscaping is an equal opportunity employer. We value a diverse and inclusive workplace and are committed to creating an environment where talented professionals can do their best work.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.