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Estimator/Inspector

HOA Talent · Chicago, Illinois, United States · 2026-07-26

Full-timemid-senior level
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About this role

YELLOWJACKET MAINTENANCE
Maintenance Services
Estimator / Inspector
Full-Time  |  Chicago, IL  |  Maintenance & Construction
About the Role
YellowJacket Maintenance is looking for a detail-oriented Estimator / Inspector to join our team. In this role, you'll write estimates and proposals, conduct property inspections, help manage our shop and vehicle fleet, and provide administrative support to our Field Construction Manager and Director of Operations. This is a great fit for someone who is organized, comfortable in the field and at a desk, and enjoys turning scope-of-work details into accurate, professional proposals that win business.
What You'll Do
Estimate & Proposal Writing
Write detailed estimates and proposals using company-standard formatting, including scope of work and pricing
Use SOW information and labor/material estimates from field personnel to price out jobs
Perform site visits or review photo documentation to independently develop scope of work and pricing
Provide supporting photo documentation where applicable
Partner with leadership to develop and use custom estimate/proposal templates by trade area
Present proposals to clients as needed, highlighting the value of the work to help close opportunities
Track open estimates (value, age, opportunity rating) and proactively follow up with clients
Manage the estimate queue and engage the Field Construction Manager as needed for SOW and pricing support
Inspections
Perform routine property inspections to identify maintenance deficiencies and verify workmanship on completed work
Produce estimates for repairs based on inspection findings
Conduct onboarding inspections for new clients to verify onsite assets and identify existing issues
Develop scope of work and pricing for preventative and reactive maintenance plans based on findings
Shop Stewardship
Manage the onsite maintenance storage area, including an inventory system for material usage, billing, and purchasing
Audit material expenses vs. revenue to help ensure profitability on purchases and billbacks
Keep the storage area organized and help technicians obtain needed equipment/materials
Assist in managing the vehicle fleet: routine inspections, condition/damage documentation, mileage tracking, service scheduling, and fuel usage tracking
Administrative Support
Support the Field Construction Manager and Director of Operations with time card review and payroll assistance
Assist with technician management and oversight
Support job costing, profitability analysis, and spend/opportunity analysis

Requirements
What We're Looking For
Strong written communication and attention to detail
Comfortable estimating from field-provided data as well as independent site visits/photos
Organized, able to manage multiple open estimates and deadlines at once
Basic understanding of maintenance/construction scopes of work and pricing
Comfortable with light fleet and inventory management responsibilities
Prior experience in estimating, inspections, or facilities/construction maintenance is a plus
Benefits
Compensation & Benefits
$65,000–$75,000 · Health/dental/vision · PTO policy ·

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