Senior Estimator (Progression to Director)
$130,000 - $160,000 + Training + Progression + Bonus + Excellent Benefits Package
Winchester, VA (Commutable from: Stephens City, Front Royal, Berryville, Middletown, Frederick County, Charles Town, Martinsburg)
Are you a Senior Estimator from a commercial construction background looking for a clear, structured pathway into Director-level leadership where your expertise and decisions will directly shape the future of the business?
On offer is a high-impact estimating role with defined progression into senior leadership. You will move beyond producing numbers alone and into influencing bid strategy, mentoring others, and contributing to long-term business growth, with support and development toward a future Director position.
This company is a well-established and highly respected commercial contractor delivering complex and high-profile projects across the region. They offer a professional, collaborative environment where senior estimators are trusted, listened to, and actively developed. You will work closely with executive leadership and be viewed as a key figure in the company's long-term succession planning.
In this role, you will lead the estimating process on commercial projects, producing accurate and competitive bids while contributing to strategic decision-making. You will review drawings and specifications, perform detailed take-offs, and support bid strategy on both hard bid and negotiated work. Over time, you will take on greater leadership responsibility, including mentoring estimators and influencing how projects are priced and delivered.
This role would suit a Senior Estimator with commercial GC experience who is ready to step into a leadership trajectory and progress toward a Director-level role.
The Role:
1. Senior Estimator within a commercial general contractor
2. Prepare detailed estimates covering labor, materials, equipment, and subcontractors
3. Lead estimating efforts on hard bid and negotiated projects
4. Review drawings, perform take-offs, and contribute to bid strategy and decision-making
The Person:
5. Estimating experience within a commercial general contractor
6. Strong understanding of construction drawings, specifications, and design
7. Self-motivated, professional, and comfortable operating at a senior level
8. Ambitious and motivated by progression into leadership and long-term influence