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IS2 Workforce Solutions

Chief Estimator

London, ON, Canada

Full-time

Apply About employer

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Job details

Job type: Full-time
Apply by: Nov 7, 2026
Experience: 8–12+ years of progressive estimating experience, preferably within commercial, industrial, or institutional construction.
Posting language: English
Posted: Oct 8, 2026

Original job description

We are seeking an experienced Chief Estimator to provide strategic leadership for a growing construction estimating function. This is a senior leadership opportunity for an accomplished estimating professional who can lead complex bids, develop high-performing estimating teams, and contribute to preconstruction and business development strategies.

The successful candidate will oversee the estimating process from concept and budgeting through tender and project handoff, ensuring estimates are accurate, competitive, commercially sound, and aligned with overall profitability objectives.

This individual will work closely with executive leadership, Operations, Business Development, clients, consultants, subcontractors, and trade partners.

Key Responsibilities

Estimating Leadership & Strategy

Lead and provide strategic direction to the estimating department, including Senior Estimators, Estimators, and Junior Estimators.
Establish and maintain estimating standards, processes, policies, and best practices.
Oversee departmental workload and resource allocation to ensure multiple bids are delivered accurately and on schedule.
Lead go/no-go bid decisions in partnership with executive leadership, evaluating project fit, capacity, risk, and profitability.
Provide executive-level guidance on bid strategy, value engineering, constructability, and alternative delivery models.
Review and approve major estimates to ensure alignment with profitability objectives, contractual requirements, and risk parameters.
Ensure estimates achieve targeted gross margins based on project type and risk profile.

Preconstruction & Bidding

Oversee conceptual budgets, schematic estimates, detailed estimates, bids, and procurement strategies for major projects.
Lead major tender closings, ensuring submissions are accurate, compliant, competitive, and strategically positioned.
Identify, assess, and manage estimating and project-related risks throughout the bidding process.
Support the transition from successful tender to Operations through structured project handoff meetings.
Ensure estimating assumptions, risk registers, subcontractor commitments, pricing strategies, and other critical information are effectively transferred to the Operations team.
Support contract negotiations through detailed cost breakdowns, scope clarification, and risk analysis.

Team Leadership & Development

Mentor, coach, and develop estimating professionals at all levels.
Establish clear performance expectations and support the professional development and advancement of team members.
Contribute to succession planning and the development of future estimating leaders.
Promote accountability, collaboration, continuous improvement, and a high-performance culture within the estimating department.

Business Development & Client Relationships

Work closely with Business Development and Operations to align estimating strategies with organizational objectives.
Serve as a senior representative with clients, consultants, developers, subcontractors, and trade partners throughout the preconstruction process.
Participate in client presentations, interviews, proposal discussions, and other business development activities.
Build and maintain strong relationships with key industry partners to support negotiated and repeat business opportunities.
Provide strategic estimating and commercial insight to support growth initiatives.

Market Intelligence & Continuous Improvement

Monitor construction market conditions, subcontractor pricing, labour costs, and material costs to improve competitiveness and forecasting accuracy.
Oversee historical cost data, benchmarking tools, and estimating databases.
Champion the adoption of estimating technologies, digital workflows, and data-driven tools that improve accuracy, efficiency, and scalability.
Lead lessons-learned initiatives and incorporate findings into estimating processes and best practices.
Monitor key departmental metrics, including bid-to-win ratios, estimate accuracy versus actual costs, and proposal quality.
Ensure estimating practices remain current with evolving construction delivery models, contract structures, and industry trends.
Participate as a member of the senior leadership team in strategic planning, annual planning, and resource planning.

Qualifications & Experience

Diploma or degree in Construction Management, Civil Engineering, Architectural Technology, or a related discipline.
8–12+ years of progressive estimating experience, preferably within commercial, industrial, or institutional construction.
Demonstrated success leading complex construction bids and estimating teams.
Proven experience managing, mentoring, and developing estimating professionals.
Strong understanding of construction methodologies, contracts, and project delivery models, including Lump Sum, Construction Management, and Design-Build.
Strong financial, analytical, and commercial acumen with exceptional attention to detail.
Proficiency with estimating and construction technology such as OST, Bluebeam, Procore, or comparable platforms.
Advanced proficiency with Microsoft Office.
Strong communication, negotiation, presentation, and relationship-management skills.
Proven ability to manage multiple complex bids and competing deadlines.
Established relationships with subcontractors, suppliers, consultants, and other construction industry stakeholders are considered an asset.

What You Bring

The ideal candidate is a strategic and commercially minded estimating leader who combines strong technical estimating expertise with exceptional leadership and relationship-building skills.

You are comfortable operating at both the strategic and detailed level - providing executive-level insight while remaining close enough to the estimating process to challenge assumptions, identify risk, and ensure quality.

You are also passionate about developing people, building strong teams, improving processes, and contributing to the long-term growth of an organization.

Why This Opportunity?

This is an opportunity to join a growing organization in a key leadership role where your expertise will directly influence project selection, profitability, preconstruction strategy, team development, and overall business growth.

The successful candidate will have the opportunity to make a meaningful impact on the estimating function while working closely with senior leadership and cross-functional teams.

Apply Today!

Apply About employer

More about this job

Responsibilities

Lead the estimating department and oversee estimates, bids, procurement strategies, risk assessment, and project handoffs to Operations. Develop the estimating team, support business development and client relationships, and improve estimating processes, tools, and performance.

Requirements

Requires a diploma or degree in a relevant construction-related discipline and 8–12+ years of progressive estimating experience, including leadership of complex bids and estimating teams. Candidates should have strong knowledge of construction methods, contracts, and delivery models, commercial and analytical skills, proficiency with estimating tools such as OST, Bluebeam, or Procore, and strong communication and negotiation abilities.

Skills

Estimating Leadership
Construction Estimating
Bid Strategy
Preconstruction
Cost Estimation
Risk Management
Value Engineering
Contract Negotiation
Team Leadership
Business Development
Market Analysis
Cost Benchmarking
Estimating Technology
Project Handoff
Commercial Acumen

Visa sponsorship

Not detected in the job text

Keywords

Construction Estimating
Chief Estimator
Preconstruction
Conceptual Budgets
Schematic Estimates
Detailed Estimates
Tendering
Procurement Strategy
Bid Strategy
Go/No-Go Decisions
Value Engineering
Constructability
Risk Registers
Project Handoff
Contract Negotiation
Lump Sum
Construction Management
Design-Build
OST
Bluebeam
Procore
Microsoft Office
Historical Cost Data
Cost Benchmarking
Subcontractor Pricing
Labour Costs
Material Costs
Estimating Databases
Bid-to-Win Ratios
Estimate Accuracy

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