Estimator/Inspector (Yellow Jacket Maintenance)

HOA Talent · Chicago, IL

Posted 8/7/2026 · last confirmed live 8/26/2026

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 ·

This role is published by HOA Talent on workable. SwiftFit is not the employer and does not accept applications.