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Senior Estimator

Chesapeake Contracting Group
Annapolis, MD Full Time
POSTED ON 2/9/2026 CLOSED ON 2/28/2026

What are the responsibilities and job description for the Senior Estimator position at Chesapeake Contracting Group?

The Sr. Estimator analyzes all project documents to determine the overall estimated cost of a project. Estimators gather, calculate and compile data to produce construction cost estimates for competitive bid proposals in a timely manner. The Estimator is also required to perform a thorough and detailed turnover of awarded projects to the project management team. Please note this position can be in our Owings Mills, Herndon, or Annapolis location.

  • Guides teams of varying sizes and expertise through the full bid lifecycle, ensuring smooth transitions and successful project handovers
  • Reviews project plans and specifications and coordinates with the team to confirm a complete and coordinated scope
  • Identify risk issues and their order of magnitude
  • Manages responses to invitations to bid
  • Performs quantity takeoff
  • Participates in conceptual budgets with oversight from manager
  • Develops Tab Sheets (scopes of work), gather subcontractor proposals, and prepare bid tabulation for own trade assignments
  • Coordinates scopes of work with bid team
  • Author qualifications/exclusions specific for each assigned trade
  • Builds effective relationships subcontractors, suppliers, and user groups that reflect and support company core values and meets or exceeds the customer's expectations
  • Develop subcontractor relationships
  • Attend subcontractor networking events

Requirements

  • Be proficient in all computer software programs used in estimating with particular emphasis on On-Screen Takeoff software particular emphasis on Bluebeam and On-Screen Takeoff
  • Possess strong mathematical and computer skills
  • Proficiency with all MS Office products (Word, Excel, Outlook)
  • Expertise in majority of trades in Divisions 2-16
  • Ability to be a team member, and work in a team environment
  • Ability to professionally communicate and perform in a highly stressed environment
  • Ability and willingness to abide by Chesapeake Contracting Group's policies and Core Values on a daily basis
  • Ability to meet deadlines and work time commensurate with workload
  • Effective oral and written communication skills

Benefits

πŸ“Œ A flexible work environment

πŸ“Œ State-of-the-art technology to get the job done

πŸ“Œ New office spaces designed for today's working environment

πŸ“Œ Great benefits including healthcare, 401K match, wellness programs

πŸ“Œ Opportunities for advancement and leadership training

Salary : $120,000 - $180,000

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