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.
VP of Operations , the Chief Estimator will lead the company's estimating function and oversee a team of estimators across Alberta.
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.
mentorship, coaching and succession planning
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.
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.
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.
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.
10+ years of estimating experience within heavy civil construction.
large-scale underground infrastructure projects , specifically watermain, sanitary sewer and stormwater work.
ground conditions, quantities, production, constructability and the practical execution of underground civil work .
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.
is an asset.
CET, Civil Engineering degree or related post-secondary education is an asset; Intermediate proficiency with Microsoft Office.




Comfortable working collaboratively with Operations, Project Management, Business Development and senior leadership.
direct underground civil infrastructure estimating experience . oil & gas, pipeline, building construction or other unrelated sectors will not be considered , as the estimating requirements and ground conditions are materially different.
Discretionary performance-based bonus
20 paid vacation days plus company closure over the Christmas period
Extended health and dental benefits fully paid by the employer
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
Prospect to join a highly tenured organization with strong internal promotion and long-term career potential
100% in-office position , with some flexibility for an experienced senior leader when required.
Headquartered in downtown Vancouver and serving clients nationally,
is one of the leading recruitment and solutions firms that specializes in the fields of IT & Technology, Engineering & Technical, Real Estate & Construction, and Accounting & Finance. We are dedicated to building great connections and creating strong opportunities within the workforce and the labor market.
We welcome and encourage applications from people of all backgrounds, including members of minority groups such as racialized individuals, people with disabilities, LGBTQ+ individuals, and Indigenous peoples. Our recruitment teams receive ongoing training on using objective criteria for evaluating candidates and other related topics to create an inclusive and welcoming environment for all.
Please note that we require all interested candidates to obtain the necessary work permits from the Government of Canada prior to submitting an application. Applications not meeting these criteria will not be considered.

📌 Chief estimator - construction (Calgary)
🏢 MatchBox Consulting Group
📍 Calgary