Estimator

About O’Hara’s Son Roofing

Since 1987, O’Hara’s Son Roofing (OSR) has provided new commercial roof construction, commercial roof replacement, commercial leak repair service, and preventative maintenance for commercial roofs. Headquartered in Chicago, IL, our team of 100+ employees is dedicated to providing quality work with a strong focus on safety and communication. 

As of 2026, OSR ranks among the Top 20 Roofing Contractors in the country. We specialize in the installation of numerous styles of roof applications and coatings. Additionally, we provide extensive roof repairs, OSHA-compliant safety items, and renewable energy solutions. 

OSR maintains branches throughout the country, providing timely service and maintenance to our partners in each region of the United States.

Join Our Dynamic Team and Embrace Our Core Values!

At O’Hara’s Son Roofing (OSR), we believe in “Putting the Pedal to the Metal,” driving our success forward by continuously improving and never settling for average work. As a family-oriented company, we embrace a "No Jerk Zone," fostering an environment of respect, support, and teamwork at every level. We value self-starters who take pride in their work, go above and beyond for the team, and seize opportunities to shape their future with us. If you share our commitment to doing all the little things well and being our customers' preferred roofing contractor, we invite you to apply.

Job Description

As an Estimator, you will play a crucial role in accurately assessing the costs and resources required for commercial roofing projects, including New Construction, Re-Roof, and Service work. Your ability to interpret project plans and specifications, perform accurate quantity take-offs, and provide reliable cost estimates will contribute to the success and profitability of our projects.

Responsibilities

1. Project Estimation:

• Review project plans, specifications, and other relevant documents to understand project requirements.

• Perform quantity take-offs for materials, labor, equipment, and other resources needed for construction.

• Utilize estimating software, databases, and historical data to develop accurate and detailed cost estimates.

• Collaborate with the project management team and suppliers to gather pricing information and validate costs.

• Analyze project risks and contingencies, considering them in the estimation process.

1. Cost Analysis and Value Engineering:

• Analyze project costs and identify opportunities for cost optimization and value engineering.

• Collaborate with the project team to explore alternative materials, construction methods, and cost-saving strategies.

• Conduct cost comparisons and evaluate the financial impact of different approaches or scenarios.

• Make recommendations to enhance project profitability while meeting quality and client requirements.

1. Bid Preparation and Submission:

• Prepare comprehensive bid proposals, ensuring they are accurate, competitive, and compliant with client requirements.

• Collaborate with the sales and business development teams to review bid documents and gather necessary information.

• Coordinate with subcontractors and suppliers to obtain pricing and support bid submissions.

• Monitor bid opportunities and deadlines, ensuring timely and complete bid submissions.

• Participate in bid review meetings, providing insights and recommendations to enhance the competitiveness of bids.

1. Supplier and Subcontractor Management:

• Identify potential suppliers and subcontractors, soliciting bids and proposals as necessary.

• Review and analyze subcontractor bids, ensuring they are complete and compliant with project requirements.

• Collaborate with the procurement team to negotiate and finalize subcontractor agreements and purchase orders.

• Establish and maintain relationships with suppliers and subcontractors, ensuring reliable and competitive pricing.

1. Documentation and Reporting:

• Prepare accurate and detailed cost breakdowns and estimates for presentation to clients and project stakeholders.

• Maintain organized and up-to-date records of all estimating activities, including bid documents, correspondence, and historical data.

• Provide regular reports and updates to management on estimating activities, project costs, and bid performance.

1. Industry Knowledge and Continuous Improvement:

• Stay updated on industry trends, construction materials, technologies, and pricing fluctuations.

• Attend industry events, seminars, and training programs to enhance estimating skills and knowledge.

• Seek opportunities for continuous improvement in estimating processes and methodologies.

1. Additional Responsibilities:

• Handle additional responsibilities and projects as assigned.

Requirements

• Bachelor's degree in construction management, engineering, or a related field (or equivalent work experience).

• Proven experience in estimating of commercial roofing projects, including Re-Roof and Service work; experience with New Construction projects in excess of 150,000 sq ft. is a plus.

• Solid understanding of construction methods, materials, and industry standards.

• Proficiency in construction estimating software and tools.

• Strong analytical and problem-solving skills, with the ability to interpret project documents and perform accurate quantity take-offs.

• Excellent attention to detail and organizational skills.

• Effective communication and interpersonal skills, with the ability to collaborate with internal teams and external stakeholders.

• Team player attitude is a must.

If you embody our core values of continuous improvement, teamwork, attention to detail, and dedication to delivering consistent, quality work, we invite you to join our team at O’Hara’s Son Roofing (OSR). Together, let's strive for excellence and be the preferred roofing contractor for our valued customers.

What OSR Offers You

• Flexible Work Environment

• Unlimited PTO + Paid Holidays

• Technology Package

• Medical Benefits - Partial Contribution:

• Medical Insurance: Aetna (EPO, PPO, & PPO HSA)

• Dental Insurance: Aetna (PPO)

• Vision Insurance: Guardian Insurance

• Retirement:

• 401k with up to 4% company match - after 1 year of continuous employment and 1000 hours worked

• Non-Contributory Benefits - Employer Paid:

• Life Insurance

• Accidental Death & Dismemberment (AD&D)

• Short Term Disability (STD)

• Long Term Disability (LTD)

• Quarterly Interactive Employee Events

About Our Hiring Process

We will share all the details on our company during the initial phone call. Maintaining your confidentiality is a priority, so your resume will only be submitted with your approval. We will keep you updated throughout each step of the hiring process. 

Please, complete our online job application and send your resume in PDF format, including a personal email address, and mobile number where we can text or leave voicemails for you during regular business hours (8-5 pm CST). We appreciate your time and consideration of this career opportunity. Please, contact us with any additional questions at hiring@oharasson.com.

The preceding job description has been designed to indicate the general nature and level of work to be performed. It is not meant to be interpreted as a comprehensive inventory of all duties and responsibilities required of employees assigned to this job.

O’Hara’s Son Roofing is an Equal Employment Opportunity and E-Verify compliant Employer. Our company is a Drug Free Workplace. Candidates must be authorized to work in the U.S.