About Cliffstone Corporation

Ryan Bennett founded Cliffstone Corporation in 2019. He is a graduate of Austin Prep and went on to get his Bachelor’s Degree at Bridgewater State University. Ryan worked as a foreman at Woolard Contracting for over 15 years along side his father, Dan Woolard, prior to acquiring Paladino Landscaping in 2017. Ryan has a wealth of knowledge in both landscape and masonry services and holds a Construction Supervisors License. His attention to detail and his willingness to work closely with each individual customer sets him apart from others in his field. Ryan is a member of the Woburn Kiwanis Club. He enjoys being on the lake in the summer and skiing in the winter. Ryan also enjoys spending time with his wife and two daughters, Riley and Taylor.

Dan Woolard owned and operated Woolard Contracting, a high-end masonry/ contracting company out of Woburn, MA for 40 years. Dan and Ryan worked together for many of those years on both large and small masonry projects. Dan, a skilled mason, brings significant experience and expertise to the masonry division at Cliffstone Corporation. Dan is a long time member and past president of the Woburn Kiwanis Club. He enjoys spending time with his family, especially his 14 grandchildren.

John graduated from Billerica Memorial High School. He worked as a roofer for a year and a half prior to being hired by Woolard Contracting in September 1989. John spent the first 4 years as a laborer (masons tender). This is where he learned the masonry trade prior to becoming a mason and working with all types of stone, brick, stucco, and concrete. In addition to masonry, John has extensive experience in the set up of scaffolding and roof staging on all types of roofs including asphalt, slate, and wood. John’s 30 years of experience provides leadership to the masonry crew and ensures that all jobs are done to perfection.