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Sierra Construction Group

Chief Estimator

Woodstock, ON, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Dec 2, 2026
Experience: 12+ years of progressive estimating experience in commercial, industrial, or institutional construction, with proven success in leading complex bids.
Posting language: English
Posted: Nov 2, 2026

Original job description

The Chief Estimator is responsible for leading the estimating department, overseeing the preparation of all bids, budgets, and cost estimates for the company’s construction projects. This role ensures accuracy, competitiveness, and profitability in all estimates while providing strategic leadership, mentoring staff, and collaborating with executives on business development and preconstruction strategies. The Chief Estimator manages the full estimating process from concept through tender, establishes best practices, and maintains strong relationships with clients, consultants, and subcontractors.

Key Responsibilities:

Provide leadership and direction to the estimating department, managing Senior Estimators, Estimators, and Junior Estimators.
Establish and enforce estimating standards, policies, and best practices to ensure consistency, accuracy, and competitiveness across all bids.
Mentor and develop estimating staff, ensuring professional growth, succession planning, and a strong pipeline of future leaders.
Manage departmental workload, balancing resources across multiple tenders to meet deadlines and client expectations.
Lead go/no-go bid decisions in collaboration with executive leadership, evaluating project fit, capacity, risk, and profitability.
Oversee the preparation of conceptual budgets, schematic estimates, detailed bids, and procurement strategies for major projects.
Review and approve all final estimates, ensuring they align with company profitability goals, contractual requirements, and risk frameworks.
Ensure estimates achieve targeted gross margins by project type.
Lead bid risk identification reviews and management efforts.
Lead major tender closings, ensuring submissions are compliant, accurate, and positioned strategically for success.
Lead the transition from successful tender to Operations through formal project handoff meetings, ensuring complete transfer of estimating assumptions, risk registers, subcontractor commitments, and pricing strategies.
Collaborate with Operations, and Business Development teams to align estimating strategies with overall company objectives.
Act as a senior contact with clients and consultants during preconstruction, supporting presentations, interviews, and proposal discussions.
Provide executive-level input on bid strategies, value engineering options, constructability reviews, and innovative delivery models.
Track and analyze market trends, subcontractor pricing, and material costs to maintain competitiveness and improve cost forecasting.
Develop and maintain productive long-term relationships with key clients, developers, consultants and trade partners to increase negotiated and repeat business opportunities.
Support contract negotiations by providing cost breakdowns, scope clarifications, and risk analyses.
Champion adoption of estimating technologies, digital workflows, and databases that improve accuracy, efficiency, and scalability.
Oversee maintenance of historical cost data and benchmarking tools to support budgeting and forecasting.
Lead lessons-learned sessions and integrate feedback into continuous improvement initiatives for the estimating function.
Monitor departmental KPIs such as bid-to-win ratios, estimate accuracy vs. actual costs, and proposal quality, reporting results to the Preconstruction Director.
Ensure estimating practices remain current with evolving delivery models, contract types, and industry innovations.
Participate in the GC leadership team, contributing to strategic, annual, and resource planning activities.
Adhere to all company policies and procedures
Perform any other duties that may be assigned, whether specifically or generally related to the role

Required Knowledge and Experience:

Diploma or degree in Construction Management, Civil Engineering, Architectural Technology, or a related field.
12+ years of progressive estimating experience in commercial, industrial, or institutional construction, with proven success in leading complex bids.
Demonstrated experience leading and mentoring estimating teams.
Strong knowledge of construction methods, contracts, and delivery models (Lump Sum, Construction Management, Design-Build).
Strong financial and analytical skills with a high degree of accuracy.
Excellent communication, negotiation, and presentation skills.
Proven ability to manage multiple bids simultaneously under tight deadlines.
Established relationships within the subcontractor and supplier community considered an asset.

Artificial Intelligence (AI) Disclosure

Sierra Construction Group does not use artificial intelligence (AI) to screen, assess, or select applicants during the recruitment and hiring process. All applications are reviewed and evaluated by members of our recruitment and hiring team.

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More about this job

Responsibilities

Lead the estimating department and oversee budgets, bids, tender submissions, risk reviews, and final estimates to support accurate, competitive, and profitable construction projects. Collaborate with executives, clients, consultants, Operations, and Business Development on bid strategy, project handoffs, staff development, market analysis, and continuous improvement.

Requirements

Requires a diploma or degree in Construction Management, Civil Engineering, Architectural Technology, or a related field, plus 12 or more years of progressive construction estimating experience. Candidates should have experience leading and mentoring teams, managing complex bids, and demonstrate strong knowledge of construction methods, contracts, delivery models, financial analysis, communication, and negotiation.

Skills

Construction Cost Estimating
Bid Management
Budgeting
Risk Management
Team Mentoring and Development
Resource Planning
Financial Analysis
Contract Knowledge
Negotiation
Preconstruction Strategy
Value Engineering
Constructability Reviews
Market and Cost Analysis
Estimating Technology Adoption

Visa sponsorship

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Keywords

Construction Estimating
Conceptual Budgets
Schematic Estimates
Detailed Bids
Tender Management
Procurement Strategies
Lump Sum
Construction Management
Design-Build
Bid Risk Reviews
Risk Registers
Gross Margins
Project Handoffs
Subcontractor Commitments
Value Engineering
Constructability Reviews
Cost Forecasting
Historical Cost Data
Benchmarking
Estimating Technologies
Digital Workflows
Bid-To-Win Ratios
Estimate Accuracy
Contract Negotiations
Preconstruction
Business Development
Commercial Construction
Industrial Construction
Institutional Construction

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