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, including building and verifying surfaces, running mass haul analyses, and identifying errors.
Expert-level proficiency in Bluebeam Revu for plan markup, quantity takeoff, multi-sheet bid documentation, and collaborative review workflows.
Proficiency 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, including muck soils, high water tables, dewatering, SJRWMD and SWFWMD regulatory context, and wet-season scheduling impacts.
Demonstrated experience pricing 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.
A proven track record of managing multiple bids simultaneously without errors or missed deadlines.
Experience leading or mentoring junior estimating staff.
Strong written and verbal communication skills, including the ability to defend estimates clearly and concisely.
Responsibilities
Lead the full bid process, including plan review, quantity takeoff, subcontractor scope leveling, final pricing, and submittal, for all active pursuits.
Perform earthwork takeoffs using Agtek and GPS-grade plan interpretation, and produce cut/fill and mass haul analyses for Florida grading projects.
Take off underground utility quantities for storm, sanitary, and water systems, and price installation using the company’s self-perform crew cost model.
Develop and maintain unit cost standards, productivity benchmarks, and pricing databases based on actual project history.
Solicit, level, and qualify subcontractor and supplier quotes for outsourced scopes, identify pricing risks, and incorporate them into estimates.
Manage overlapping bid deadlines across multiple simultaneous pursuits while maintaining accuracy.
Mentor and review junior estimating staff and build accuracy and accountability within the estimating department.
Conduct post-project cost analyses by comparing estimated and actual costs, and incorporate lessons learned into future bids.
Collaborate with project managers and field superintendents to ground estimates in real-world conditions and crew production rates.
Manage and organize bid documentation, plan files, and estimate archives in SharePoint.
Coordinate team communication and bid workflow through Microsoft Teams.
Represent the company in pre-bid meetings, site walks, and client interactions related to scope and pricing.
Desired Qualifications
Experience with HCSS HeavyBid or an equivalent estimating platform.
WHITES SITE DEVELOPMENT Central Florida · Civil Site Development Now Hiring: Senior Chief Estimator
Senior Level · 10+ Years Experience · Orlando / Central Florida Metro
ABOUT WHITES SITE DEVELOPMENT
Whites Site Development is a Central Florida-based civil site development company specializing in multifamily and commercial ground-up projects. We operate a high-performance, lean platform — an integrated general contractor and civil engineering entity — built to deliver complex site work on schedule and on budget. 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
This is the top estimating seat at Whites Site Development. The Senior Chief Estimator owns the full bid workflow — from plan review through final number — and is responsible for the accuracy, competitiveness, and profitability of every estimate that leaves this company.
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
This role requires someone who has done it at a high level for a long time. No learning curve on the fundamentals.
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
Every WSD hire is evaluated against five values. These are not aspirational — they are the standard:
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
Send your resume and a brief note (3–5 sentences) describing your most complex Florida estimating win — what made it hard and how you priced it — to: