SITE SUPERVISOR SITE SUPERVISOR
Produced by Matt Gorgolinski CEO and Founder
Big League Talent Co.
Winchester is a specialized high-end residential builder based near Annapolis.
A revered and respected partner, Winchester serves their clients and award-winning architects in Maryland, Washington, D.C., and the Eastern Shore. Winchester understands that fine building is indeed an art. The firm’s artistry results from clarity of purpose, collaboration with renowned architects, integration of seasoned professionals, and the highest standards for quality construction. The workmanship and durability of a Winchester-built home resonates for generations.
Winchester’s capabilities are boundless as evidenced by the range of scope, size and style of its commissions.
Uncompromising quality, attention to detail, and toplevel craftsmanship have resulted in the construction of rustic villas, traditional and historic homes, contemporary homes, weekend retreats, and country estates.
The firm has earned trust from clients and architects alike as well as accolades from the design and construction industry. Winchester places great value on the relationships that are created and sustained through the construction process.
The company ’ s team consists of carpenters, masons, and painters; a concrete and excavation crew, field supervisors, and project managers. In addition, longstanding relationships with subcontractors enable the execution of consistent quality work to be performed at the level set by Winchester.
The Residence Management division continues the client relationship long after a home is completed, offering support for preventative maintenance, general maintenance and repairs, and minor renovation work to any home built by the firm. Each member of Winchester’s team understands the vital role they play and is committed to the satisfaction of the client and maintaining the integrity of the architecture.
VALUES
Professionalism and Integrity
Every employee, whether on the job site or in the office shares this commitment to professional excellence.
Attention to Quality and Detail
From craftsmanship to communications, attention to detail is essential. The result is an exceptional home that achieves the vision of the homeowner and is built to provide enjoyment for generations to come.
Teamwork and Cooperation
Building or renovating a home involves countless details and decisions. Teamwork among Winchester’s staff combined with the close collaboration and regular communication with the homeowners, architects, and designers ensures a cohesive, coordinated approach.
PROCESS
Vision
A custom home may not be for everyone. The decision, however, to invest the necessary time, resources, and energy toward building or renovating a one-of-a-kind residence will yield a lifetime of pleasure.
Planning
The beginnings of a custom home bring the homeowner, the architect, and the builder together to work on a project that may take several months to several years. The hallmarks of a successful collaboration are shared commitment, mutual trust, and open lines of communication throughout the process.
Construction
Winchester’s president, Michael Campbell, keeps an eye on every project with support from project managers, who are the primary contacts for every client from start to finish. A field supervisor coordinates the daily construction activities on site. Winchester’s project managers and field supervisors have years of experience, know every phase of the construction process, and enjoy working in an environment focused on superior quality and uncompromising client service.
Teamwork
Winchester is one part of a dedicated team. The best results come from close collaboration and cooperation among all parties involved in a project. Winchester is committed to giving homeowners, architects, and other professionals such as landscape architects and interior designers the same level of cooperation and support.
Details
Other than construction quality and design, the most significant element that separates the custom homebuilding process from standard construction is a greater level of detail. The same characteristic separates Winchester from many other builders, whether on the job or in the office.
Completion
As the project nears completion, the excitement builds. Rough concrete and wood framing give way to finished walls, honed surfaces, and custom trim.
Seeing a home’s beauty and potential no longer requires imagination the quality can be experienced at every turn.
Service
Durability through design, material selection, and construction are the first steps in creating a home that will last for generations. Dedicated maintenance is the key to promoting longevity of any structure.
SITE SUPERVISOR
Location: Annapolis, MD
Compensation: $120,000 – $185,000
Winchester Construction has spent over four decades quietly earning a reputation as the MidAtlantic’s most trusted high-end custom builder.
Based near Annapolis, the firm is known for its unrelenting commitment to craftsmanship, its respectful collaboration with some of the country’s most elite architects and interior designers, and its ability to deliver residences that feel timeless from the moment they’re complete.
This is a builder’s builder. One that honors design integrity. That believes in clarity of purpose. And that treats every project as a generational investment—for both the client and the team executing it.
With over 500 completed homes spanning rustic waterfront villas, historic renovations, modern retreats, and traditional estates, Winchester’s portfolio reflects not a single aesthetic, but a standard: uncompromising quality, down to the last detail.
At the heart of the firm are its people skilled tradespeople, seasoned supervisors, and quietly exceptional project managers—who execute with pride and professionalism. With a team that selfperforms key trades and a Residence Management division that supports clients long after move-in, Winchester has built more than homes. They’ve built trust.
We’re now hiring a Site Supervisor to join this legacy.
ROLE OVERVIEW
As a Site Supervisor at Winchester, you’ll lead day-to-day operations on active job sites, coordinating internal crews and long-trusted subs while representing the firm’s values and execution standards.
You’ll oversee every detail—foundation to final finish—with an eye for quality, an appreciation for architectural intent, and the judgment to solve challenges calmly and collaboratively.
You’ll be trusted to lead, empowered to own outcomes, and supported by a team that values people who do things the right way.
YOUR TOOLKIT
10+ years in custom home or estate-scale residential construction
Mastery of sequencing, site safety, and subcontractor management
Strong communication with architects, homeowners, and PMs
Hands-on familiarity with finishes, framing, and MEP coordination
Calm under pressure. Clear under deadlines. Built for field leadership.
WHAT YOU’LL GET
$120,000 to $185,000 salary
Performance-based bonus
Full benefits (medical, dental, vision, 401k)
Vehicle allowance or company truck
Access to stunning builds and true craftspeople
Long-term career path, rooted in trust, mentorship, and legacy
This search is retained and exclusive—Winchester Construction has partnered with us to find the right fit.
If you ’ re ready to build something that lasts with a team that does too reach out to learn more.
