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.

• 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…