Matthew Dempsey

Matt is a strategic, solutions-focused Project Executive with almost 30 years of experience leading complex institutional and commercial construction projects. As a former business owner, he brings a comprehensive understanding of construction operations, preconstruction and project delivery, with a proven ability to guide clients through every phase of the building process. His expertise spans higher education, advanced technology, life science, residential and corporate headquarters projects throughout southeastern Massachusetts and Rhode Island.

As a Project Executive, Matt leads projects from planning through completion, partnering closely with clients and project teams to establish project objectives, direct preconstruction efforts and ensure successful execution. He is responsible for aligning project strategy with Timberline’s standards for quality, performance and client service, while helping teams navigate complex challenges and deliver exceptional results. Matt also works to standardize preconstruction frameworks and delivery processes that improve stakeholder alignment, reduce schedule risk and support informed decision-making throughout the life of a project.

Prior to joining Timberline, Matt served as an owner and partner of a regional construction firm, where he oversaw enterprise-wide operations including safety, estimating, procurement, finance and field execution. Throughout his career, he has worked extensively with colleges, universities and independent schools, including Harvard, Boston College, Brown and Dartmouth, while also delivering projects for clients in the advanced technology, life science, residential and corporate sectors. At Timberline, Matt’s broad operational expertise and collaborative leadership style position him to help clients successfully deliver their most complex projects.

Matt earned a Bachelor of Science in Engineering with a minor in Entrepreneurship from Rensselaer Polytechnic Institute. He holds a Massachusetts Unrestricted Construction Supervisor License and OSHA 30 certification and was recognized as a Providence Business News 40 Under 40 honoree. Known for bringing structure to complexity, building high-performing teams and fostering strong client relationships, Matt’s leadership, operational expertise and commitment to collaboration make him a valuable addition to Timberline’s Senior Leadership Team and an important contributor to the firm’s continued growth and success.