Assistant Insurance Restoration Contractor Jobs in Alsip, IL

Join Our Team as an Exterior Construction Estimator

Exterior Construction Estimator – Roofing & Insurance Restoration

Skyline Construction | Northwest Indiana

Full-Time | Office + Field Position

Skyline Construction is seeking a knowledgeable, detail-oriented Exterior Construction Estimator to join our growing team. This hands‑on position combines field inspections, office estimating, insurance restoration documentation, and ongoing file management.

The ideal candidate understands exterior construction, works confidently in Xactimate, communicates consistently, and takes ownership of each file from inspection through estimating and supplemental documentation.

Key Responsibilities: Field Inspections and Measurements

• Travel throughout Northwest Indiana and the surrounding service area for property inspections
• Safely climb ladders and access residential roofs
• Inspect roofing, siding, gutters, soffit, fascia, flashing, ventilation, and other exterior components
• Identify storm damage, construction issues, and required repairs or replacement
• Accurately measure exterior components, elevations, slopes, quantities, and materials
• Use Hover and other measurement technology to create and verify property measurements
• Compare digital reports with actual field conditions
• Take clear, organized photographs and document all relevant job details
• Gather sufficient information during the initial inspection to prepare a complete estimate

Insurance Restoration and Estimating

• Prepare detailed estimates using Xactimate
• Review insurance carrier estimates, scopes of work, and claim documents
• Compare carrier scopes and measurements with Skyline’s field findings, Hover reports, and actual property conditions
• Identify inaccurate measurements, missing items, incorrect quantities, waste calculations, pricing, and line items
• Recognize necessary accessories and components, including flashing, ventilation, underlayment, siding components, and detach/reset items
• Prepare contractor supplements based on Skyline’s scope, documentation, material requirements, code requirements, and pricing
• Submit supporting photographs, measurements, reports, and other documentation
• Communicate professionally with insurance representatives regarding Skyline’s scope, quantities, documentation, and pricing
• Maintain accurate records throughout the estimating and supplemental process

This role requires more than transferring information into Xactimate. You must understand exterior construction well enough to recognize when a scope, measurement, or estimate is incomplete or inaccurate.

Communication and File Management

• Keep JobTread and related files consistently updated
• Record clear notes, file status, conversations, and next steps
• Manage multiple estimates and insurance files simultaneously
• Follow up on outstanding items and communicate delays or problems proactively
• Respond to customers, coworkers, insurance representatives, and leadership in a timely, professional manner
• Keep the team informed of information affecting scheduling, estimating, and project responsibilities

Technology

• Xactimate
• Hover
• JobTread
• Email and Google Workspace
• PDFs, insurance documents, and photo/document management systems
• AI tools for research, documentation, organization, and productivity

Strong computer, typing, email, and document‑management skills are required. Experience with every program is not necessary, but Xactimate experience is strongly preferred. Candidates with strong exterior construction knowledge and the ability to learn quickly may be considered without prior Xactimate experience.

Qualifications

• Exterior construction knowledge, including roofing, siding, gutters, soffit, fascia, flashing, ventilation, underlayment, and related components
• Ability to accurately measure properties, calculate materials, and document field conditions
• Understanding of manufacturer requirements; building code and insurance restoration experience are preferred
• Strong written and verbal communication skills
• Excellent organization, attention to detail, and follow-through
• Ability to work independently, solve problems, make decisions, and manage changing priorities
• Professional customer-service skills
• Comfort working both in the field and at a computer
• Valid driver’s license and reliable transportation
• Local residence in Northwest Indiana or a reasonable commuting distance
• Ability to drive locally for inspections and appointments
• Ability to safely climb extension ladders and walk residential roofs
• Dependability, punctuality, and willingness to ask questions when information does not make sense

Preferred Experience

• Xactimate
• Insurance restoration estimating and supplements
• Reviewing carrier scopes
• Hover, JobTread, EagleView, or similar measurement systems
• Roofing, siding, or gutter installation
• Exterior construction project management
• Building codes and manufacturer specifications

About Skyline Construction

Skyline Construction is a family‑owned exterior construction company serving Northwest Indiana and the Chicagoland area. We specialize in roofing, siding, gutters, soffit, fascia, and related exterior construction.

We value accuracy, communication, accountability, teamwork, and follow-through and are looking for someone who wants to become an important part of our team.

Schedule

Full-Time

Primarily weekday hours combining office work and field inspections. Some flexibility may be required based on customer appointments, weather, storm events, active projects, and workload.

Compensation and Benefits

Competitive compensation based on construction knowledge, Xactimate experience, insurance restoration experience, and overall qualifications.

Skyline Construction offers:

• Paid time off
• Paid holidays
• Opportunities for performance‑based bonuses
• Additional benefits planned as the company continues to grow

If you understand exterior construction, enjoy solving problems, work well with technology, and take pride in accurate estimating and clear communication, we would like to hear from you.

By applying to this job, you agree to receive periodic text messages from this employer and Homebase about your pending job application. Opt out anytime. Msg & data rates may apply. Powered by Homebase. Free employee scheduling, time clock and hiring tools.