Our History

Caldwell Constructors, Inc. was founded on May 5, 2005 by Gary F. Caldwell. After working with a few exceptional construction companies in the Upstate of South Carolina for 29 years, Gary decided it was time to venture out on his own. With extensive experience in commercial, institutional, ecumenical and industrial market segments, and management experience in both estimating and operations with these firms, the foundation was in place to begin a new company within the vibrant community of Greenville, SC.

Our initial clients were individuals and firms with whom Gary built relationships over the years. Through the recommendations of those key members of the community, we quickly developed a substantial client base. The company’s goal was to grow slowly as a result of selecting the right projects and scope that we could manage effectively, while producing exceptional and consistent results for our clients. Subcontractors and vendors have been instrumental in our success as well.

We appreciate their response and commitment to our approach to meeting our clients’ needs. The company has experienced very controlled and intentional growth since inception. We are very proud of our staff that includes the addition of talented, qualified and energetic personnel that share our core values and who are committed to our mission of providing exceptional service and value to our clients.

“We could not have asked for a more responsive and adaptable team as your fine firm, and the people really are most talented and easy to work with. We are getting compliments on the renovations hourly, not daily, which speaks of the fine work done.”
– Tommy McAfee, Thomas McAfee Funeral Homes

Our Mission:

To become the most sought-after contractor in the Upstate by providing exceptional service through unwavering integrity, creative problem solving and a tireless work ethic.

Core Values:

Integrity: Always do the right thing above all else
Honesty: Be honest no matter the consequences
Respect: Respect everyone and treat them as equal
Service: Keep the client’s needs first
Communication: Provide effective and efficient communication throughout the process

Our Team

Gary Caldwell



Gary brings over 40 years of experience to the commercial construction industry of the Upstate. In 2005, Gary founded Caldwell Constructors where he revels in opportunities to provide simplicity to complex builds. His unparalleled integrity is built from a strong history of community and charitable involvement with organizations like Habitat for Humanity, Cancer Society of Greenville County, Leukemia and Lymphoma Society, the Poinsett Club, the Chamber of Commerce and Leadership Greenville. His passion and innovative approach to projects make him an incredible asset to the construction industry within the Upstate of South Carolina. Gary has the pleasure of working alongside his son David, daughter Amanda and nephew Brett. In his free time, he enjoys spending time with his wife, Leigh, and their four grandchildren as well as kayaking and hunting.

David Caldwell

VP of Operations

David provides over 10 years of experience to Caldwell Constructors where he proudly follows his father’s footsteps and is a shareholder. He is passionate about providing top-notch quality service and helping local businesses with their commercial construction needs. David graduated from Clemson University’s Construction Science and Management program and after school spent time in both single-family and multi-family residential construction. David lives in Greenville with his wife Allison and their two young daughters. In his free time, he enjoys hunting and spending time in the great outdoors.

Brett Caldwell

VP of Preconstruction

With nearly 20 years of construction experience, Brett has made a huge impact working alongside his uncle and cousins at Caldwell Constructors. After graduating from Clemson, Brett began his construction career working on complex nine-figure commercial projects along the Eastern seaboard. He began at Caldwell Constructors in 2005 and is now a shareholder and a LEED Accredited Professional. Brett resides in Greenville with his wife Rachell and their two sons. He enjoys staying active while playing tennis and hiking.

Chris Norris

Senior Project Manager

Chris brings over 20 years of commercial construction experience in medical, senior housing, and higher education projects. He graduated from Clemson University and from there, went on to manage projects throughout the Carolinas with individual contracts valued over $60 million. Chris is married to his wife Lorian and has three daughters. In his free time, he enjoys watching Clemson football and playing golf.

Evan Jones

Project Manager

Evan has almost 15 years of construction experience as he began his career working with his grandfather’s construction company in Abbeville, SC. Equipped with a finance degree from Wofford College and valuable project management experience, Evan is a crucial part of the Caldwell Constructors team. Outside of work, Evan spends his time with his wife Natalie and their three sons. He enjoys sport fishing, wing shooting, archery and coaching youth athletics.

Stephen Watkins

Project Manager

Stephen proudly brings over 30 years of construction experience in the Upstate to Caldwell Constructors. After receiving his degree from Clemson, he started his own company and worked for other local companies over the years. Stephen’s impressive background in all facets of construction include conventional commercial projects, multi-million-dollar industrial buildings and pre-engineered metal buildings. Both Stephen and wife Emily are Greenville natives and enjoy doing life with their 2 daughters. In his free time, he enjoys the lake, craft markets, traveling and watching Clemson football.

Richard Heath

With over 35 years of experience, Richard has worked as a carpenter, superintendent, project manager, business owner, and estimator. Most recently he served as a Senior Estimator with a local commercial construction company. Richard currently serves as the National Director of the Professional Construction Estimators Association Upstate Chapter. Richard enjoys hiking through the Upstate mountains, trail biking, fly fishing and motorcycle touring.

Ben Chubb

Assistant Project Manager

Since joining the Caldwell Constructors team in May of 2019, Ben brings almost 2 years of experience in the field. He is a recent graduate from Mississippi State University’s Building Construction Science program and has worked with multiple companies assisting in both private and commercial projects. He thrives while being on-site and watching project progress first-hand. In his free time, Ben enjoys the outdoors, fishing and hiking.

Zach Miles

Zach is a graduate from the Construction Science and Management department at Clemson University. While attending Clemson, he served as the president of the National Association of Home Builders student chapter and earned his LEED GA certification. Outside of work, he is an avid outdoorsman, mountain biker, and Clemson football fan.

Amanda O’Sullivan


Amanda brings ten years of experience to Caldwell Constructors. As a shareholder, she proudly contributes to the family business with her father, brother and cousin. She graduated from Clemson and now oversees the accounting department and is responsible for all finances, corporate budgeting, and human resources. Apart from work, she enjoys spending her free time with her husband, Ryan, and their two children. She enjoys traveling, monogramming and other creative outlets.

Britain Means

Operations Administrator

Britain has over ten years of experience in commercial construction. She graduated from Auburn with a degree in Building Science and served as an on-site project manager for large commercial projects across the Southeast. After relocating to Greenville, she joined Caldwell Constructors to help streamline operational procedures and manage workflow. Britain is married to her husband Greg and has one daughter. In her free time, she enjoys gardening and reading.

Rebecca Castles


Rebecca brings eight years of construction experience to the Caldwell Constructors team. She graduated from the College of Charleston and began her construction career after working as a missionary in Tennessee. She ensures the office is running smoothly and in her free time, enjoys spending time with her husband Earl and their two children.

Holly Wood

Contract Administrator

Holly provides over 30 years of professional experience to Caldwell Constructors. Since beginning her career in 1989, Holly has proven to be an experienced professional with expertise in federal and state regulatory requirements, budget and financial management. In her spare time, Holly enjoys spending time with her husband Jeff, who also works alongside the Caldwell team as a superintendent, and their three daughters.