Chief Estimator

Our client is a well-established, privately held Ontario construction company with more than 30 years of experience. The organization has grown from strong civil and infrastructure roots into a diversified construction platform with capabilities across General Contracting, Construction Management, Design-Build, Infrastructure, Bridges, Aggregates and Land Development. Its General Contracting portfolio includes commercial, industrial, institutional and multi-residential projects throughout Ontario.

The Chief Estimator will lead the estimating function and take ownership of the quality, competitiveness, risk profile and profitability of bids from early-stage budgeting through tender and handoff to Operations. This is a hands-on leadership role for an accomplished construction estimator who can combine technical depth with team leadership, commercial judgment and strategic thinking.

Key Responsibilities

• Lead, mentor and develop the estimating team, including Senior Estimators, Estimators and Junior Estimators.
• Oversee the full estimating process from conceptual budgeting through tender close, ensuring accuracy, competitiveness and alignment with targeted margins.
• Establish and continuously improve estimating standards, policies, best practices, historical cost data and departmental KPIs.
• Lead go/no-go reviews with senior leadership, assessing project fit, resource capacity, commercial risk and profitability.
• Review and approve conceptual budgets, schematic estimates, detailed bids, procurement strategies and major tender submissions.
• Lead constructability reviews, value engineering, risk assessment and bid strategy for complex projects.
• Ensure disciplined project handoff to Operations, including assumptions, exclusions, risk items, subcontractor commitments and pricing strategy.
• Build and maintain strong relationships with clients, consultants, developers, subcontractors and suppliers.
• Partner closely with Operations, Preconstruction and Business Development throughout pursuit, award and transition phases.
• Champion estimating technology and digital workflows, including tools such as Procore, Bluebeam and takeoff/estimating platforms.

Qualifications and Experience

• Post-secondary education in Construction Management, Civil Engineering, Architectural Technology or a related discipline.
• 12+ years of progressive estimating experience within commercial, industrial and/or institutional construction.
• Proven experience leading complex bids and managing or mentoring an estimating team.
• Strong knowledge of Lump Sum, Construction Management and Design-Build project delivery models.
• Demonstrated understanding of subcontractor markets, procurement strategy, cost planning and construction risk.
• Strong financial, analytical, negotiation, communication and presentation skills.
• Ability to work effectively with senior leadership, operations teams, clients and external partners.
• Experience with Procore, Bluebeam and modern estimating/takeoff technology is an asset.

What Will Make You Successful

• You are a proven estimating leader, not simply a strong individual contributor.
• You can challenge assumptions, identify commercial risk and protect margin without losing competitiveness.
• You are comfortable leading major bid closings and presenting recommendations to executives.
• You develop people and create consistent, repeatable estimating practices.
• You understand how strong preconstruction and estimating decisions affect project execution and profitability.

Why Consider This Opportunity

This is a senior leadership opportunity with an established Ontario contractor offering a strong project platform, competitive executive-level compensation and the ability to influence how major construction work is planned and delivered.

Disclosure:

This posting represents an active and genuine vacancy with one of 3 Step Recruitment’s clients and is not for speculative or pipeline recruitment.

3 Step Recruitment and/or our Clients may use, from time to time, AI-assisted tools to support the screening and evaluation of applications; however, these tools are not intended to replace human judgement or decision-making in the hiring process.