Chief Estimator in Calgary

MatchBox Consulting Group is seeking a Chief Estimator to join a well-established heavy civil contractor in Calgary, Alberta. Our client is a long-standing Alberta contractor with deep expertise in underground infrastructure, watermain, sewer, stormwater, earthworks and complex civil construction. With operations across Alberta, the organization has built a strong reputation for successfully delivering challenging projects and is trusted by major general contractors, municipalities and other established industry partners. This is an opportunity to join a stable, highly tenured organization where leadership development, internal promotion and long-term relationships are central to the culture.

About the Role

Reporting to the VP of Operations, the Chief Estimator will lead the company's estimating function and oversee a team of estimators across Alberta. This position will have cradle-to-grave ownership of the estimating function, including estimating strategy, bid development, risk review, team leadership, process improvement and the transition of successful bids into operations. The Chief Estimator will also be part of the senior leadership group, contributing to strategic planning, business development and decisions around which opportunities the company pursues. The estimating team is experienced but continuing to develop, making mentorship, coaching and succession planning important parts of the role.

Key Responsibilities

• Lead and oversee estimating activities across multiple Alberta offices and markets.
• Review project opportunities and determine estimating and pursuit strategies.
• Lead the preparation, review and submission of competitive estimates for major heavy civil projects.
• Develop bid strategies focused on winning work while maintaining appropriate margins and managing project risk.
• Review quantities, pricing, production assumptions, constructability, ground conditions and other key estimating considerations.
• Work closely with General Managers, Operations and Project Management teams during bid development and bid day.
• Identify contractual, commercial, constructability and execution risks and communicate them to senior leadership.
• Develop and improve estimating systems, processes, procedures and best practices across the organization.
• Lead contract review and estimating-to-operations handoff processes.
• Mentor, coach and develop estimators while supporting training and succession planning.
• Manage and improve subcontractor and vendor relationships, coverage and prequalification processes.
• Improve bid scoping, subcontractor coverage and overall estimate development practices.
• Develop conceptual estimating tools and databases to improve the speed and accuracy of early-stage estimates.
• Lead the implementation, maintenance and ongoing improvement of estimating technology, including B2W.
• Collaborate with Business Development on RFQs, RFPs, strategic pursuits and client relationships.
• Participate in market analysis, strategic account planning and industry networking.
• Work with General Managers and senior leadership to identify target opportunities and develop strategies to win them.
• Support client discussions around project costs, timelines, design requirements and constructability.
• Participate in due diligence and early project development activities, including coordination with external consultants when required.
• Contribute to corporate business planning, financial objectives and process improvement initiatives.
• Provide senior leadership with reporting and insight into bidding activity, opportunities and market conditions.
• Participate as a member of the leadership team and contribute to broader organizational initiatives.

Qualifications & Experience

• 10+ years of estimating experience within heavy civil construction.
• Proven experience estimating large-scale underground infrastructure projects, specifically watermain, sanitary sewer and stormwater work.
• Strong understanding of ground conditions, quantities, production, constructability and the practical execution of underground civil work.
• Previous leadership, team management or mentorship experience.
• Ability to read and interpret drawings, specifications and contract documents and develop accurate cost estimates.
• Strong understanding of project risk, contractual requirements and bid strategy.
• Experience with B2W and/or Bluebeam is an asset.
• CET, Civil Engineering degree or related post-secondary education is an asset; equivalent industry experience will be considered.
• Intermediate proficiency with Microsoft Office.
• Strong communication, organization, time management and prioritization skills.
• Comfortable working collaboratively with Operations, Project Management, Business Development and senior leadership.
• This role requires direct underground civil infrastructure estimating experience. Candidates whose background is primarily oil & gas, pipeline, building construction or other unrelated sectors will not be considered, as the estimating requirements and ground conditions are materially different.

What’s Offered

• Discretionary performance-based bonus
• 20 paid vacation days plus company closure over the Christmas period
• Group RRSP matching program
• Extended health and dental benefits fully paid by the employer
• Company vehicle with fuel card or $1,500/month vehicle allowance
• Primarily Calgary-based, in-office position with flexibility for senior-level needs
• Limited travel, generally under 20%, including occasional trips to Edmonton, Lethbridge and project sites
• Opportunity to join a highly tenured organization with strong internal promotion and long-term career potential

Location

This is a 100% in-office position, with some flexibility for an experienced senior leader when required.