Senior Chief Estimator
Orlando, FL
Full Time
Senior Manager/Supervisor
WHITES SITE DEVELOPMENT
Central Florida · Civil Site Development
Now Hiring: Senior Chief Estimator
Central Florida · Civil Site Development
Now Hiring: Senior Chief Estimator
Senior Level · 10+ Years Experience · Orlando / Central Florida Metro
ABOUT WHITES SITE DEVELOPMENT
We are growing rapidly. Our estimating function is the engine of that growth, and we are hiring a Senior Chief Estimator to lead it.
THE ROLE
You will work directly with the Executive Director and Vice President on strategy and bid selection. You will oversee a junior estimating team, develop pricing standards, and carry the institutional knowledge of how WSD prices work. This is a high-accountability role for a proven professional who has been in the field and knows what things actually cost.
WHAT YOU'LL DO
- Lead the full bid process — plan review, quantity takeoff, sub scope leveling, final pricing, and submittal — for all active pursuits
- Perform earthwork takeoffs using Agtek and GPS-grade plan interpretation; produce cut/fill and mass haul analysis for Florida grading projects
- Take off underground utility quantities (storm, sanitary, water) and price installation using WSD's self-perform crew cost model
- Develop and maintain unit cost standards, productivity benchmarks, and pricing databases based on WSD's actual project history
- Solicit, level, and qualify subcontractor and supplier quotes for outsourced scopes; identify pricing risk and incorporate appropriately
- Manage overlapping bid deadlines across multiple simultaneous pursuits without sacrificing accuracy
- Mentor and review the work of junior estimating staff; build a culture of accuracy and accountability in the estimating department
- Conduct post-project cost analyses — compare estimated vs. actual — and incorporate lessons learned into future bids
- Collaborate directly with project managers and field superintendents to ground estimates in real-world conditions and crew production rates
- Manage and organize all bid documentation, plan files, and estimate archives in SharePoint; coordinate team communication and bid workflow through Microsoft Teams
- Represent WSD professionally in pre-bid meetings, site walks, and client interactions related to scope and pricing
WHAT WE'RE LOOKING FOR
- 10+ years of civil site work estimating experience, with demonstrated success on multifamily and commercial ground-up projects in Florida
- Expert-level proficiency in Agtek earthwork software — you build and verify your own surfaces, run your own mass haul, and catch errors before anyone else does
- Expert-level proficiency in Bluebeam Revu — plan markup, quantity takeoff, multi-sheet bid documentation, and collaborative review workflows
- Proficient in Microsoft SharePoint for bid file organization, document management, and team collaboration; daily use of Microsoft Teams for internal coordination, bid communication, and project team workflow
- Thorough understanding of Florida site conditions: muck soils, high water table, dewatering, SJRWMD and SWFWMD regulatory context, wet season scheduling impacts
- Demonstrated experience pricing both self-perform crew labor and outsourced subcontracted scopes on the same bid
- Familiarity with FDOT standards, FDOT pay items, and DOT-adjacent or municipal project estimating
- HCSS HeavyBid or equivalent estimating platform experience strongly preferred
- Proven track record managing multiple bids simultaneously without errors or missed deadlines
- Experience leading or mentoring junior estimating staff
- Strong written and verbal communication skills — you can defend your numbers clearly and concisely
CORE VALUES WE HIRE FOR
- Reliability — your estimates are accurate, your deadlines are met, and your team can count on you
- Transparency — you surface risks, flag scope gaps, and communicate problems early
- Accountability — when a number is off, you own it, learn from it, and fix it
- Company First — you put the bid and the team ahead of your own convenience
- Resourcefulness — you solve problems with incomplete information and you don't wait to be told what to do
WHAT WE OFFER
- Senior leadership role with direct access to the Executive Director and VP
- Competitive base compensation commensurate with experience — this is a top-of-market position for the right candidate
- A lean, high-performance team where your work is visible and your impact is direct
- A growing platform with a clear path to department leadership as the company scales from $25M to $50M
- Central Florida's most interesting civil site work — multifamily, commercial, mixed-use — with complex scopes that reward sharp estimators
HOW TO APPLY
Whites Site Development · Central Florida · whitessitedevelopment.com
Equal Opportunity Employer
Equal Opportunity Employer
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