Head Estimator & Bid Strategy Leader

Sierra Construction; Woodstock; On-site; CAD 120,000 - 180,000; Full time

Job summary

Sierra Construction is seeking a Chief Estimator to lead the estimating department, oversee bids, budgets, and cost estimates for complex projects, ensuring accuracy, competitiveness, and profitability.

The role partners with executives on preconstruction strategies, mentors staff, and drives best practices, tools adoption, and value engineering. You will manage multiple tenders and coordinate with Operations, Business Development, and clients.

Qualifications

• 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.
• 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.

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

Skills

Estimating leadership

Team mentoring

Financial analysis

Communication

Negotiation

Presentation skills

Bid management

Education

Construction/Engineering degree

Job description

Sierra Construction is seeking a Chief Estimator to lead the estimating department, oversee bids, budgets, and cost estimates for complex projects, ensuring accuracy, competitiveness, and profitability.

The role partners with executives on preconstruction strategies, mentors staff, and drives best practices, tools adoption, and value engineering. You will manage multiple tenders and coordinate with Operations, Business Development, and clients.