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Posted 2 months ago

Chief Estimator

@ Sierra Construction

Woodstock, Ontario

12+ years experience
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SIGNALS

Overview

Sierra Construction is hiring a Chief Estimator to lead the estimating department and oversee all bids, budgets and cost estimates for its construction projects. The role manages senior and junior estimators, leads bid go/no-go decisions with executives, and hands successful tenders to Operations.

Responsibilities:

  • Lead and mentor the estimating department
  • Approve final estimates and margins by project type
  • Lead go/no-go bid decisions and tender closings
  • Manage handoff from successful tender to Operations
  • Track market trends and subcontractor pricing

Requirements summary:

  • Diploma or degree in construction management, civil engineering or architectural technology
  • 12+ years of progressive commercial, industrial or institutional estimating experience
  • Experience leading and mentoring estimating teams
  • Strong knowledge of lump sum, CM and design-build delivery
  • Strong financial and analytical skills
  • Subcontractor and supplier relationships considered an asset

Tools & skills

Source and dates

Employer career site / ATS feed · greenhouse

Employer posting date
2026-08-28
First seen by our source
2026-10-08
Source record updated
2026-10-14

These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.

Job details

SenioritySenior
DepartmentBusiness development
Experience12+ years
Manages peopleYes
Work settingOffice, Client sites
PositionMostly sitting
Physical demandsphysical low · computer high
LanguagesEnglish
EducationCollege diploma (required), Bachelor’s degree (required)
Fields of studyConstruction Management, Civil Engineering, Architectural Technology

Summary and details written by AI from the posting; the employer’s posting is the authority.

Sierra Construction

Saved company profile

Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.

General Contracting | Bridge | Infrastructure | Land Development

Full company description

Sierra Construction is an independently-owned and managed Construction Firm based in Woodstock, Ontario. From our beginnings in Infrastructure, we’ve grown to include professional divisions focused on Design-Build, Construction Management, General Contracting, Bridges, and Aggregates to better serve customers across Ontario. Our reputation is only as good as our last project. Working with our network of consultants, suppliers, and subcontractors, our experienced team creates project plans that meet your needs and deliver work that exceeds your expectations.

LinkedIn followers
19,179
People associated on LinkedIn
103
Reported office locations
  • 1193 Dundas Street, P.O. Box 20053, Woodstock, Ontario N4S 8X8, CA
Other recorded names
  • Sierra Construction
  • Sierra Construction Group
Specialties
  • Construction Management
  • Design/Build
  • Civil Construction
  • General Contracting
  • Land Development
  • and Preconstruction
Profile identifies a recruitment agency
No

Sierra Construction is an independently-owned and managed Construction Firm based in Woodstock, Ontario. From our beginnings in Infrastructure, we’ve grown to include professional divisions focused on Design-Build, Construction Management, General Contracting, Bridges, and Aggregates to better serve customers across Ontario. Our reputation is only as good as our last project. Working with our network of…

FieldValue
IndustryConstruction
Company size51-200 employees
HeadquartersWoodstock, Ontario
Organization typePrivately Held
Year founded1994
SpecialtiesConstruction ManagementDesign/BuildCivil ConstructionGeneral ContractingLand Developmentand Preconstruction
Open jobs on Jobsy5
LinkedInView page
Job description

The Chief Estimator is responsible for leading the estimating department, overseeing the preparation of all bids, budgets, and cost estimates for the company’s construction projects. This role ensures accuracy, competitiveness, and profitability in all estimates while providing strategic leadership, mentoring staff, and collaborating with executives on business development and preconstruction strategies. The Chief Estimator manages the full estimating process from concept through tender, establishes best practices, and maintains strong relationships with clients, consultants, and subcontractors.

Key Responsibilities:

  • Provide leadership and direction to the estimating department, managing Senior Estimators, Estimators, and Junior Estimators.
  • Establish and enforce estimating standards, policies, and best practices to ensure consistency, accuracy, and competitiveness across all bids.
  • Mentor and develop estimating staff, ensuring professional growth, succession planning, and a strong pipeline of future leaders.
  • Manage departmental workload, balancing resources across multiple tenders to meet deadlines and client expectations.
  • Lead go/no-go bid decisions in collaboration with executive leadership, evaluating project fit, capacity, risk, and profitability.
  • Oversee the preparation of conceptual budgets, schematic estimates, detailed bids, and procurement strategies for major projects.
  • Review and approve all final estimates, ensuring they align with company profitability goals, contractual requirements, and risk frameworks.
  • Ensure estimates achieve targeted gross margins by project type.
  • Lead bid risk identification reviews and management efforts.
  • Lead major tender closings, ensuring submissions are compliant, accurate, and positioned strategically for success.
  • Lead the transition from successful tender to Operations through formal project handoff meetings, ensuring complete transfer of estimating assumptions, risk registers, subcontractor commitments, and pricing strategies.
  • Collaborate with Operations, and Business Development teams to align estimating strategies with overall company objectives.
  • Act as a senior contact with clients and consultants during preconstruction, supporting presentations, interviews, and proposal discussions.
  • Provide executive-level input on bid strategies, value engineering options, constructability reviews, and innovative delivery models.
  • Track and analyze market trends, subcontractor pricing, and material costs to maintain competitiveness and improve cost forecasting.
  • Develop and maintain productive long-term relationships with key clients, developers, consultants and trade partners to increase negotiated and repeat business opportunities.
  • Support contract negotiations by providing cost breakdowns, scope clarifications, and risk analyses.
  • Champion adoption of estimating technologies, digital workflows, and databases that improve accuracy, efficiency, and scalability.
  • Oversee maintenance of historical cost data and benchmarking tools to support budgeting and forecasting.
  • Lead lessons-learned sessions and integrate feedback into continuous improvement initiatives for the estimating function.
  • Monitor departmental KPIs such as bid-to-win ratios, estimate accuracy vs. actual costs, and proposal quality, reporting results to the Preconstruction Director.
  • Ensure estimating practices remain current with evolving delivery models, contract types, and industry innovations.
  • Participate in the GC leadership team, contributing to strategic, annual, and resource planning activities.
  • Adhere to all company policies and procedures
  • Perform any other duties that may be assigned, whether specifically or generally related to the role

Required Knowledge and Experience:

  • Diploma or degree in Construction Management, Civil Engineering, Architectural Technology, or a related field.
  • 12+ years of progressive estimating experience in commercial, industrial, or institutional construction, with proven success in leading complex bids.
  • Demonstrated experience leading and mentoring estimating teams.
  • Strong knowledge of construction methods, contracts, and delivery models (Lump Sum, Construction Management, Design-Build).
  • Strong financial and analytical skills with a high degree of accuracy.
  • Excellent communication, negotiation, and presentation skills.
  • Proven ability to manage multiple bids simultaneously under tight deadlines.
  • Established relationships within the subcontractor and supplier community considered an asset.

#INDHI

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