Match Box 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 secure, 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 B2 W.
Collaborate with Business Development on RFQs, RFPs, strategic pursuits and client relationships.
Participate in market analysis, strategic

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