Search Jobs

Location: Greater Boston, MA | Schedule: Full-Time, On-Site | Compensation: $150,000–$180,000 + Bonus & Excellent Benefits

Overview

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.

What you'll do

• 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

Required 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
• Strong organizational skills with the ability to manage multiple high-profile pursuits simultaneously

Preferred qualifications

• Design-Build and Joint Venture estimating experience is highly desirable

Compensation and 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

Why this role

Join an established contractor with an excellent reputation in the heavy civil market, leading a talented estimating team on landmark infrastructure projects while working directly with senior leadership on strategic growth, backed by a strong backlog of public work and long-term stability.