Estimating Director

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 the Estimating Director, you will helm the critical task of forecasting the costs, resources, and timelines necessary for our new construction projects. Your expertise in construction estimating and strong analytical skills will shape the operational success of our projects. Leading the estimating team, you will enhance our daily operational workflows, ensuring precision and efficiency in all estimating activities.

Responsibilities

• Strategic Estimation Leadership:

• Spearhead the development and refinement of estimation strategies, aligning them with both short-term project goals and long-term organizational objectives.

• Analyze market trends, historical data, and the competitive landscape to enhance bidding success rates.

• Innovate and implement advanced estimating techniques, tools, and software, ensuring the new construction estimators remain at the forefront of technological advancements in the industry.

• Ensure detailed cost projections for new construction projects, including labor, materials, equipment, and subcontractor costs.

• Analyze and quantify project risks and contingencies.

• Collaborate with the estimating and project management teams to refine and finalize project estimates.

• Team Management and Development:

• Cultivate a culture of excellence and continuous improvement within the estimating team by setting clear performance objectives, providing regular feedback, and facilitating professional development opportunities.

• Organize regular training sessions to ensure the team is proficient in the latest estimating software, understands current market pricing, and is aware of new roofing materials and techniques.

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

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

• Cost Analysis and Value Engineering:

• Conduct detailed feasibility studies for each new project to assess the complexity, potential challenges, and unique requirements.

• 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.

• Develop a systematic approach for reviewing and updating estimates at key project milestones or when significant changes occur, ensuring estimates remain accurate and relevant.

• Vendor and Subcontractor Liaison:

• Develop and maintain a preferred vendor and subcontractor program, evaluating performance based on quality, reliability, and cost-effectiveness, to foster long-term partnerships.

• Implement a transparent and fair bidding process for subcontractors and supplies, encouraging competition and innovation, and ensuring the best value for the company.

• Reporting and Documentation:

• Develop a dashboard or reporting system that provides real-time insights into estimating activities, bid status, and project margins, accessible to senior management and key stakeholders.

• Ensure comprehensive documentation of all estimation processes, decisions, and justifications, maintaining a robust audit trail for future reference and continuous improvement.

• 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.

• Participate in project handover meetings, ensuring effective transfer of estimating information to the project execution team.

• Risk Management:

• Introduce advanced risk assessment tools and methodologies to quantify potential risks, developing mitigation strategies for identified risks.

• Regularly review and update risk management practices to address emerging threats and opportunities in the construction landscape.

• Industry Engagement:

• Act as the company’s ambassador in industry forums, engaging with peers, thought leaders, and innovators to share knowledge and bring back insights that can drive the company forward.

• Foster a culture of learning and innovation within the team by encouraging participation in external training programs, workshops, and seminars relevant to commercial roofing and construction estimating.

• Additional Responsibilities:

• Handle additional responsibilities and projects as assigned.

Requirements

• Bachelor's degree in construction management, engineering, quantity surveying, or a related field. Advanced degrees or certificates in estimating or project management are a plus.

• Minimum of 7 years of experience in construction estimating, with at least 3 years in a leadership role, preferably in commercial roofing or construction industry.

• Expertise in various construction estimating software and platforms specific to construction and roofing.

• Strong financial and analytical skills, with the ability to accurately interpret complex project plans and specifications.

• Demonstrated leadership abilities with experience in team development and performance management.

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

• Team player attitude is a must.

• Ability to manage multiple projects and deadlines in a fast-paced environment.

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 [email protected].

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.