Chief Estimator – Heavy Civil & Bridge Construction

Keystone Distinction Group; Boston (MA); On-site; USD 150,000 - 180,000; Full time

Benefits offered by this job

Competitive base salary

Bonus program

Excellent benefits

Job summary

Keystone Distinction Group in Greater Boston seeks a seasoned Chief Estimator to lead the bridge and heavy civil estimating team and shape preconstruction strategy for major transportation projects in New England.

The role requires 15+ years in heavy civil and proven leadership in public infrastructure estimates, with expertise in Design-Build and JV opportunities. Collaboration with exec leadership and operations is essential to drive growth and project success.

Qualifications

• 15+ years of experience in heavy civil, bridge, or transportation construction.
• Previous experience as Chief Estimator, Estimating Manager, Director of Estimating, or Senior Lead Estimator.
• Experience with estimating projects valued at $50M+.
• Strong leadership, communication, and team development skills.
• Design-Build and Joint Venture estimating experience is highly desirable.
• Strong organizational skills with ability to manage multiple high-profile pursuits simultaneously.

Responsibilities

• Evaluate bidding opportunities and prioritize project pursuits.
• Lead the estimating process from opportunity review through bid submission.
• Develop estimating schedules, assign resources, and maintain workload balance.
• Direct estimate reviews and oversee bid-day activities.
• Identify project risks and develop appropriate pricing strategies.
• Lead estimating efforts for Design-Build and Joint Venture opportunities.
• Build and maintain strong relationships with subcontractors, suppliers, and industry partners.
• Coordinate estimating handoff during the post-award transition to operations.
• Recruit, mentor, and develop estimating staff.
• Work closely with project management, operations, and executive leadership.
• Support business development initiatives and strengthen client relationships.
• Continuously improve estimating procedures, systems, and best practices.

Skills

Estimating leadership

Team development

Project management

Stakeholder communication

Preconstruction strategy

Public infrastructure

Mentoring staff

Risk assessment

Tools

HCSS HeavyBid

B2W

Primavera P6

Microsoft Project

Job description

Chief Estimator – Heavy Civil & Bridge Construction

Greater Boston, MA | Full-Time | $150,000–$180,000 + Bonus & Excellent Benefits

A well-established, rapidly growing heavy civil contractor is seeking an experienced Chief Estimator to lead its Bridge and Heavy Civil estimating team. This is a key leadership role responsible for driving the preconstruction process, developing estimating talent, and helping shape the company's long-term growth strategy.

The successful candidate will oversee complex public infrastructure pursuits, collaborate closely with executive leadership and operations, and play a critical role in securing major transportation and infrastructure projects throughout New England.

Responsibilities

• Evaluate bidding opportunities and prioritize project pursuits.
• Lead the estimating process from opportunity review through bid submission.
• Develop estimating schedules, assign resources, and maintain workload balance.
• Direct estimate reviews and oversee bid-day activities.
• Identify project risks and develop appropriate pricing strategies.
• Lead estimating efforts for Design-Build and Joint Venture opportunities.
• Build and maintain strong relationships with subcontractors, suppliers, and industry partners.
• Coordinate estimating handoff during the post-award transition to operations.
• Recruit, mentor, and develop estimating staff.
• Work closely with project management, operations, and executive leadership.
• Support business development initiatives and strengthen client relationships.
• Continuously improve estimating procedures, systems, and best practices.

Qualifications

• 15+ years of experience in heavy civil, bridge, or transportation construction.
• Previous experience as a Chief Estimator, Estimating Manager, Director of Estimating, or Senior Lead Estimator.
• Demonstrated success managing complex public infrastructure estimates valued at $50M+.
• Strong leadership, communication, and team development skills.
• Experience with estimating software such as HCSS HeavyBid, B2W, Primavera P6, Microsoft Project, or similar platforms.
• Design-Build and Joint Venture estimating experience is highly desirable.
• Strong organizational skills with the ability to manage multiple high-profile pursuits simultaneously.

Compensation & Benefits

• Competitive base salary: $150,000–$180,000, depending on experience.
• Performance-based bonus program.
• Comprehensive medical, dental, and vision insurance.
• 401(k) with company match.
• Generous PTO, paid holidays, and sick leave.
• Vehicle or mileage reimbursement.
• Cell phone allowance.
• Long-term career advancement with a respected and financially stable infrastructure contractor.