Chief/Director of Estimating

Added - 08/26/26 Chief/Director of Estimating Construction & Real Estate Chicago , Illinois | Direct Hire

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Position: Chief of Estimating
Reports To: Chief Executive Officer
Location: Chicago, Illinois — in-seat leadership presence required
Travel: Periodic travel to regional offices and project pursuits as needed
Compensation: Competitive and commensurate with experience (Director through Vice President level). The total-rewards package includes base salary, an annual performance bonus, and employee stock ownership (ESOP).
Chamberlain Advisors is conducting an executive search on behalf of Richard Group, a fast-growing, employee-owned national general contractor delivering vertical construction across a diversified set of sectors, including federal, civic, education, healthcare and wellness, advanced technology and industrial, and residential and multifamily. Founded and led by Jed Richard, the firm is scaling rapidly toward multiple billions in annual construction volume and is centralizing its estimating function into a single, technology-enabled source of truth. The Chief of Estimating is a foundational leadership hire charged with building that centralized cost cell, mentoring a young and talented estimating team, and instilling the discipline and systems that will support the firm’s next chapter of growth.

Core Profile: alignment with the following is required to get you in the conversation

• Master Communicator, High EQ & Empathetic In-Seat Mentor (Go / No-Go): You will be a crystal-clear communicator with exceptionally high emotional intelligence — this is the single explicit, non-negotiable requirement for the role. You will serve as a physical, in-seat leader and empathetic mentor to a team of eight to nine early-career estimators who have operated without strong in-seat leadership, checking in weekly, putting an arm around a shoulder, and consistently building people up. You will translate cost intelligence cleanly and confidently to your team, to peers in operations, and directly to the CEO. This role calls for a leader who brings a team along as naturally as they command the numbers — estimating skill alone will not carry it without the steadiness, openness, and generosity to elevate the people around you.
• Estimating Mastery Across Building Types & Trades: You will bring deep, hands-on estimating mastery and the ability to render a defensible opinion of cost anywhere in the country, across building types and trades — steel, carpentry, MEP systems, and ductwork — rather than merely relaying subcontractor pricing, and you will carry the independent cost sense to challenge the subcontractor market and push back on numbers that do not hold up. You will teach junior estimators to calculate a widget of steel, a mechanical system, or a run of ductwork from first principles, multiplying cost specialists across the team and establishing yourself as the technical authority the department has lacked.
• Dual Bid-Type Experience — Hard-Bid & Negotiated: You will have lived on both sides of the pursuit: the hard-bid public side — rip-and-read war-room bid days, taking twenty subcontractor numbers into the sheet in the final seconds, and knowing large-business and small-business calculations cold — and the negotiated, owner-directed private side where most private work sits. Public experience need not be federal specifically; municipal work such as City of Chicago, CTA, or FAA counts. Genuine exposure to both sides is what this role calls for.
• Scalable Estimating Technology & Systems Architecture: You will own the modern estimating technology stack, moving the team off siloed, individually owned spreadsheets and onto scalable, open-API, off-the-shelf systems — the estimating equivalent of Procore — spanning digitized and AI-assisted takeoff, an estimating platform such as Sage Timberline, a nationalized invite-to-bid platform, and a national cost database, all integrated to the ERP. You will act as a systems architect who configures out-of-the-box tools and understands how they interconnect, forecasting a five- to ten-year technology horizon rather than pursuing bespoke innovation for its own sake.
• Disciplined Win-Rate Track Record, Scale Pedigree & Cultural Fit: You will bring a disciplined, high-win-rate track record and the scale pedigree of a firm large enough to have built the systems Richard is standing up, along with an entrepreneurial, team-first temperament suited to an employee-owned firm operating with autonomy under direct CEO line-of-sight. You will commit to a consistent in-seat Chicago presence and orient to the firm’s long-term ownership and incentive horizon. You will stay in the costing lane and master the number, sharing your work and knowledge openly, scaling the people around you, and partnering behind a unified leadership team.

Core Responsibilities & Scope of Work

Centralized Estimating Leadership & Executive Partnership

• Single Source of Truth: Lead and centralize the estimating function as a single, defensible source of truth for cost intelligence, pricing accuracy, and budget development across all sectors and building types.
• CEO Partnership: Partner directly with the Chief Executive Officer and operations leadership to align budgets with project strategy, providing clear cost reporting, win-rate analytics, and recommendations that support confident, profitable growth.
• Standards & Integrity: Set, standardize, and continuously improve estimating standards, tools, templates, and processes to ensure consistency, pricing integrity, and defensible opinions of cost across the organization.
• Cost, Not Preconstruction: Own the assembly of the number — quantity takeoffs, cost modeling, pricing, subcontractor analysis, bid leveling, and budget development — distinct from preconstruction, which remains embedded with the program managers in operations.

Estimating Execution Across Conceptual, Negotiated & Hard-Bid Pursuits

• Full-Spectrum Pricing: Oversee quantity takeoffs, cost modeling, and pricing analysis for conceptual, negotiated, and hard-bid pursuits, providing defensible opinions of cost across building types and geographies.
• Conceptual Budgeting: Develop early-stage conceptual budgets alongside developers and owners using benchmarks and historical data, delivering the cost clarity that guides feasibility and early decisions.
• Subcontractor Analysis: Direct subcontractor pricing analysis, bid leveling, and estimate validation, holding an informed self-perform opinion of trade pricing that challenges the subcontractor market rather than passing through numbers that do not make sense.
• Multi-Sector Coverage: Run hard bids and negotiated pursuits across the firm’s multi-sector model — federal, civic, education, healthcare and wellness, advanced technology and industrial, and residential and multifamily.
• Clean Handoff to Operations: Deliver each number to operations in a usable, defensible format — a clear account of exactly what scope is captured, what was discussed with the estimating team, and what the price truly represents — so program managers can compare it against their own scope build and write subcontractor contracts with confidence.

Estimating Technology, Systems Architecture & Cost Data

• Stack Ownership: Lead the selection, implementation, and integration of scalable, open-API estimating technology — takeoff, estimating, invite-to-bid, and cost-database platforms — that connect to one another and to the ERP.
• Off Excel, Onto Systems: Move the team off siloed, individually owned spreadsheets and onto connected systems, sequencing the rollout tool-by-tool with a disciplined change-management and communication cadence rather than a bulldoze-everything approach.
• Cost Databases: Establish and maintain cost databases, templates, and estimating systems, and track estimate results versus actuals — capturing data from losses as well as wins in a usable, organized form — to drive continuous improvement in estimating intelligence.
• Future-Proofing: Forecast a five- to ten-year technology horizon so systems are not re-torn-up in short order, configuring out-of-the-box solutions to minimize manual intervention while securing buy-in from leadership and internal technologists.

Bidding Discipline, Win-Rate Growth & Subcontractor Analytics

• Bid Less, Win More: Rebuild bidding discipline and improve win rate — pursuing a “bid less, win more” philosophy of fewer, better-chosen pursuits rather than volume for volume — moving the function toward a materially higher win rate over time.
• Analytics Prize: Build subcontractor performance analytics — who bids, who is genuinely competitive, and who wins — to inform invite-to-bid strategy and sharpen the firm’s trade-partner engagement.
• Cost Tracking: Establish direct and indirect cost tracking tied to each estimate to strengthen accuracy, enable post-bid analysis, and connect estimates to actual project outcomes.

Post-Bid Discipline & Miss Detection

• Post-Bid Discipline & Miss Detection: Run a true post-mortem on every pursuit — completing the analysis on a lost bid within roughly a week rather than letting ego or embarrassment close the book on it, and surfacing missed numbers on won work during buyout, within two to three months, rather than during construction when it is too late to recover — and capture what is learned so it strengthens future bids.

Volume Forecasting

• Volume Forecasting: Forecast future estimating volume and resourcing needs, advising leadership on where to invest and where to add regional cost and subcontractor resources. On pursuit selection, serve as a trusted influencer rather than the decision-maker — quickly bracketing the likely cost range and flagging when an owner’s budget ceiling or a thin subcontractor market would preclude a win, so the CEO and program managers can decide what is worth chasing.

Team Leadership, Mentorship & Governance

• In-Seat Mentorship: Develop, mentor, and lead a team of estimators — senior estimators, estimators, conceptual estimators and cost planners, and cost-database analysts — providing in-seat coaching and a disciplined communication cadence.
• Teach From First Principles: Teach estimators to calculate trade costs from first principles across steel, carpentry, MEP systems, and ductwork, growing the next generation of senior estimators and cost specialists.
• Career Pathways: Provide career coaching to direct reports in support of the firm’s career pathways, and develop and deliver estimating orientation and training that scales talent as the company grows.
• Discipline & Cadence: Instill a culture of accuracy, discipline, and continuous improvement, establishing the communication cadence, reviews, and governance that make the centralized function reliable to operations — driving depth of estimate coverage rather than surface-level coverage.

Qualifications

• Minimum of fifteen years of progressive estimating experience in commercial and vertical construction, with roughly fifteen to twenty-plus years preferred and a profile in the vicinity of a proven best-athlete leader.
• Demonstrated leadership of a team of at least five true estimators running cost databases and estimating software rather than siloed spreadsheets.
• Estimating mastery across building types and trades — steel, carpentry, MEP systems, and ductwork — with the ability to render a defensible opinion of cost anywhere in the country.
• Proven ability to teach junior estimators to calculate trade costs from first principles rather than relaying subcontractor pricing.
• Hands-on experience across BOTH hard-bid work (public, federal, and municipal — including war-room bid days and large-business/small-business calculations) AND negotiated, owner-directed private work.
• Fluency in scalable, open-API, off-the-shelf estimating technology — takeoff, estimating, invite-to-bid, and cost-database platforms — and a track record of moving a team off siloed spreadsheets onto connected systems.
• Experience integrating estimating platforms with an ERP (for example, Sage Timberline/Estimating, on-screen takeoff, and invite-to-bid platforms).
• Demonstrated record of disciplined, high-win-rate bidding and of leading process and systems change with a strong communication cadence.
• Conceptual-cost command — the ability to quickly bracket a defensible cost range and speak to the primary cost drivers and owner budget expectations across sectors (for example, multifamily by door and data centers by megawatt) — that informs pursuit selection.
• Background at a large, top-tier construction organization with the scale to have built and operated scalable estimating systems and databases.
• Crystal-clear communicator with exceptionally high emotional intelligence — an empathetic, in-seat mentor who builds people up.
• Experience across multiple sectors, such as federal, civic, education, healthcare and wellness, advanced technology and industrial, and residential and multifamily.
• Chicago-based, with a consistent in-seat leadership presence (an exceptional out-of-market candidate may be considered with a strong majority in-seat presence).
• Bachelor's degree in Construction Management, Engineering, Architecture, Quantity Surveying, or a related field preferred.
• Command of both estimating and preconstruction (a “one-two punch”) a plus, though not required.

About Richard Group

Richard Group is an employee-owned national general contractor delivering vertical construction across a diversified portfolio of sectors, including federal, civic, education, healthcare and wellness, advanced technology and industrial, and residential and multifamily. Founded and led by Jed Richard, the firm has built its reputation on technical excellence, disciplined execution, and a genuine ownership culture in which every employee shares in the value they help create.
Now scaling rapidly toward multiple billions in annual construction volume, the firm is centralizing its estimating function into a single, technology-enabled source of truth and rebuilding bidding discipline to win more of the right work. The Chief of Estimating represents one of the most significant leadership hires the organization has made. For the right leader, the role offers the rare opportunity to build a centralized cost cell from the ground up, mentor a talented young team, and operate with direct line-of-sight to a hands-on CEO for whom estimating is a personal passion — all within an employee-owned firm at an inflection point in its growth.