Executive Team

Diane Dorr, President

Diane holds a marketing management and communications degree from the University of Vermont's Business School. In 2002 she launched Carefree Cape, Inc. This took place after spending a few years general contracting and remodeling in Falmouth, Cape Cod as somewhat of a career change. To augment her business degree and management experience, prior to launching Carefree Cape, Diane and a few in her management team spent a great deal of time researching, traveling and taking courses in the property management / concierge business.

Diane's earlier career included 10 years of working for a marketing consortium in Boston, MA then as a marketing manager for a large, fast-paced technology company in Waltham, MA. In the early 1990s, Diane founded a successful marketing communications firm in Sudbury, MA specializing in high tech marketing. She ran this firm for seven years before relocating to Cape Cod in 1999. Her marketing firm produced worldwide programs, published magazines and developed outstanding long-term working relationships with leading companies including IBM, Sun Microsystems, PTC, and Silicon Graphics.

Peter Dorr, Vice President, Engineering

Peter earned his computer software engineering degree from WPI and has nearly 20 years of leadership experience in the field, specifically code writing in the CAD and Web arenas. Peter is known for examining a situation or technology, identifying inefficiencies, then writing software to make the programs and people significantly more productive. He has initiated and developed programs that have won national customer service awards several times. Peter has been a loyal key employee of a large, rigorous software company in the Boston area for 19 years. His expertise has provided Carefree Cape clients with simple internet camera access to view their cape properties -- anytime, anywhere.

Brian J. O'Rourke, Construction Superintendent

Brian joined the Carefree Cape Executive team in December of 2005. He received his Bachelor of Arts in History at St. Anselm's College and is a licensed construction superintendent. Brian began his impressive 40-year construction career as a labor foreman for a large Boston-based commercial construction company. Most recently, Brian has planned and overseen residential construction and renovation projects in Falmouth, MA and provided Falmouth Hospital with the intense preconstruction statement of conditions upgrade for JCAHO inspection of their recent renovation. Brian is incredibly easy to work with. He has earned a stellar reputation in the field for quality and timeliness. In addition to overseeing residential projects, his diverse range of construction experience includes being fully responsible for the design and building of complex research and manufacturing facilities, hi-rise offices and fast-track commercial projects. Brian is now managing the day-to-day activities of residential construction and renovation projects for Carefree Cape clients. He develops material and site logistics, works with and schedules trade contractors, ensures quality and productivity of workers and workmanship. The best time to involve Brian is at the beginning stage of a project -- before working with an architect. However, his advice and expertise are invaluable at any stage.