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: Applications without the note will not be prioritized. We review on a rolling basis and respond promptly to qualified candidates.

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