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 j…
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Sign up with Clera and we'll reach out the moment a role actually fits you — no more spraying applications into the void.
$65k–$75k/yr
Full-time
Health Insurance, Dental Insurance, Vision Insurance, Paid Time Off
Posted 1d ago
~40 hrs/week
Responsibilities
The role involves writing detailed estimates and proposals, conducting property inspections to identify maintenance needs, and managing the company's shop inventory and vehicle fleet. Additionally, the position provides administrative support for payroll, job costing, and technician oversight.
Requirements
Candidates should have strong written communication skills, attention to detail, and the ability to manage multiple deadlines. Prior experience in estimating, inspections, or facilities maintenance is preferred along with a basic understanding of construction pricing.
Full job description
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
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
We exist to connect HOA industry professionals with management companies that believe in sustainable careers.
Industry
Real Estate
Company size
2-10 employees
Founded
2023
Headquarters
Chicago, IL
LinkedIn followers
330
Too many association management companies grind down their Managers with no support system and no thanks for their late nights and early mornings. But it doesn't have to be that way. We exist to connect HOA industry professionals with management companies that believe in sustainable careers.
Offices: Chicago, IL 60642, US · Washington, DC, US · Herndon, VA, US · Greenbelt, MD, US · Jacksonville, FL, US
How many Trades jobs are open in Chicago, IL right now?
There are currently 1,601 open trades positions in Chicago, IL listed on Clera. New openings are added daily as companies post roles.
Which companies are hiring for Trades roles in Chicago, IL?
Companies currently hiring include AutoZone, S&C Electric Company, Compass Group, ABM Industries, Lowe's Companies, Inc., among others. Browse the listings above to see every active employer.
Are there remote or hybrid Trades jobs in Chicago, IL?
Yes — 52 of the 1601 open trades positions offer remote or hybrid work (21 remote, 31 hybrid).
How do I apply for Trades jobs in Chicago, IL?
Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.