Chief Estimator – Commercial Specialty Contractor
Location: Jessup, MD
Job Type: Full-Time
Compensation: $150,000 – $175,000 base salary, plus performance-based bonus potential
About the Opportunity
A well-established commercial specialty contractor in the Mid-Atlantic region is seeking an experienced Chief Estimator to lead its estimating department. This is a leadership role responsible for managing a team of estimators, overseeing bid strategy, reviewing proposals, supporting business development efforts, and ensuring accurate, competitive, and profitable estimates across a wide range of commercial and government construction projects.
The ideal candidate will bring deep construction estimating experience, strong leadership skills, and a proven background in specialty contracting, civil/site work, fencing, perimeter security, concrete, masonry, or general contracting.
This role is best suited for a hands-on estimating leader who can manage people, review complex bids, improve estimating processes, and partner closely with operations, sales, and executive leadership.
Key Responsibilities
- Lead, manage, train, and mentor a team of estimators
- Oversee the full estimating process from initial bid review through final proposal submission
- Review takeoffs, scopes, vendor/subcontractor quotes, exclusions, assumptions, and bid packages for accuracy and completeness
- Develop and maintain estimating standards, workflows, templates, and best practices
- Review plans, specifications, drawings, addenda, and project requirements
- Prepare, review, and submit competitive bids and proposals for commercial, institutional, government, and public-sector construction projects
- Support business development efforts by assisting with client presentations, proposal strategy, pricing discussions, and deal closure
- Work closely with project management, operations, sales, and executive leadership to ensure estimates align with production capabilities and profitability goals
- Evaluate risk, constructability, labor requirements, material costs, subcontractor pricing, and project schedules
- Assist with onboarding and training junior estimators
- Track bid results, analyze win/loss data, and recommend process improvements
- Maintain strong relationships with general contractors, government agencies, vendors, suppliers, subcontractors, and internal teams
Qualifications
- 8+ years of construction estimating experience required
- Current or recent experience as a Chief Estimator, Senior Estimator, Estimating Manager, Director of Estimating, or Preconstruction Manager
- Prior experience managing or mentoring estimating teams required
- Strong commercial construction estimating background
- Experience with specialty contracting, civil construction, site work, fencing, perimeter security, concrete, masonry, paving, landscaping, or general contracting strongly preferred
- Experience estimating government, federal, institutional, school, highway, multifamily, or public-sector projects preferred
- Strong knowledge of takeoffs, bid preparation, scope review, proposal writing, and construction pricing
- Proficiency with Bluebeam Revu required
- Experience with estimating software such as HCSS HeavyBid, Sage Estimating, ProEst, On-Screen Takeoff, PlanSwift, or similar platforms preferred
- Familiarity with government procurement, prevailing wage, Davis-Bacon requirements, DoD, GSA, or federal project requirements is a plus
- Ability to lead estimating strategy while remaining hands-on with details
- Strong communication, leadership, organization, and decision-making skills
- Must be local to the Greater Baltimore/DC region or within a reasonable commute to Jessup, MD
Preferred Background
Candidates with experience in any of the following areas are strongly encouraged to apply:
- Commercial specialty contracting
- Commercial general contracting
- Government or federal construction
- Institutional, school, highway, or public-sector work
Compensation & Benefits
- Base salary of $150,000 – $175,000, depending on experience
- Performance and profitability-based bonus opportunity
- Full-time leadership role with long-term growth potential
- Opportunity to lead and develop an established estimating team
- Work on high-profile commercial, institutional, and government-related construction projects
Schedule
- Monday to Friday
- Full-time
- In-person role based near Jessup, MD
Location Requirement
This is a local position. Candidates should be based within commuting distance of Jessup, MD, including the Greater Baltimore, Columbia, Annapolis, Washington DC, or Northern Virginia areas.
Equal Opportunity
The employer is an equal opportunity employer and encourages qualified candidates from all backgrounds to apply. Veterans and individuals with military service are strongly encouraged to apply.
Pay: $150,000.00 - $175,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Health insurance
- Paid time off
- Vision insurance
Work Location: In person
