For 30 years, Sleeping Dog Properties has stood out as an award-winning general contractor in the Greater Boston Area. The company has built a reputation for tackling some of the area’s most complex and demanding construction projects, including high-rise penthouses, healthcare facilities, modern restaurants, and traditional brownstones. 

Sleeping Dog Properties has risen to prominence in a competitive construction market thanks to the forward-thinking leadership of Founder and President Chris Rapczynski. Rapczynski has always prioritized the well-being of his team and community over the numbers on a balance sheet, earning him the trust of local customers and the loyalty of the area’s most talented contractors and skilled workers. 

While Rapczynski’s vision laid the foundation for Sleeping Dog Properties, he has always acknowledged that the efforts of his leadership team are the true secret to the company’s success. Together, they’ve transformed Sleeping Dog Properties into one of New England’s premier construction firms.

Sleeping Dog Properties: The Team Behind the Dream

Sleeping Dog Properties’ diverse and talented team is behind each of its bespoke construction projects and renovations. Meet the SPD’s award-winning leadership team to learn how strong, community-driven leaders are critical for success in general contracting.  

Chris Rapczynski: President & Founder

Chris Rapczynski is the Founder and President of Sleeping Dog Properties. For the past 30 years, he has driven the company’s growth and success. 

Rapczynski’s journey began as a carpenter and tradesman in Boston. He developed a reputation as one of the most honest contractors in the area. Not only did he meet his construction goals, but he respected his clients by treating them with kindness and charging fair rates. 

Demand for his services quickly grew, and he established Sleeping Dog Properties in 1993. Under his leadership, the company has managed over $500 million in projects across luxury residential, boutique commercial, and unique hospitality properties. Rapczynski’s commitment to quality, honesty, and community continues to set the tone for the entire company. 

Derrick Tyler: COO

As the Chief Operating Officer of Sleeping Dog Properties, Derrick Tyler manages the company’s day-to-day operations. Tyler’s journey with the company began in 2003 when he started as an intern while pursuing his Bachelor of Architecture at the Wentworth Institute of Technology. Over the years, he climbed the ranks from Designer to Project Manager to COO. 

Thanks to Tyler’s diverse roles at the company over the years, he has a complete understanding of all aspects of construction and the needs of his staff.   

Tyler’s responsibilities include overseeing contract negotiations, project management, and financial controls. He’s not afraid to get his hands dirty, and, like Chris Rapczynski, he prioritizes time spent on-site with the SDP team. Tyler’s hands-on leadership has been instrumental in maintaining the company’s client-first approach, central to Sleeping Dog’s success.

Joe Boccelli: Director of Construction

Director of Construction Joe Boccelli brings a lifetime of experience in the local construction industry to Sleeping Dog Properties. 

Bocelli grew up in a construction family where he learned the value of hard work, quality craftsmanship, and practical problem-solving from a young age. Over his 20+ year career, he has overseen projects totaling over $150 million in residential and commercial sectors.

Boccelli’s success at SDP stems from his knowledge of all things construction. He can seamlessly transition between roles as a site supervisor, project manager, and estimator—all within the same day. 

Like Rapczynski, Boccelli is strongly connected to his on-site teams and dedicated to his community. His ability to build relationships with customers and contractors has been key to Sleeping Dog Properties’ success.

Michael Feldman: Controller

As the Controller of Sleeping Dog Properties, Michael Feldman is the company’s financial backbone. He brings over 30 years of experience in financial leadership roles in the real estate and construction industries. 

His accounting and financial management expertise ensures that the company’s projects remain financially viable. Feldman’s meticulous approach to finances and his knowledge of construction have helped SDP find innovative ways to deliver top quality at fair rates. He works closely with Chris Rapczynski to maintain the company’s core value of putting community before profit. 

Chris Rapczynski’s Honest Approach to Leadership

Chris Rapczynski started his career with a hammer hanging off his belt and a saw in his hand. He understands that quality work results from more than training and education. It comes from a passion for the job and compassion for your team. 

For this reason, Rapczynski believes in investing heavily in his staff. To maintain a top-tier team, he pays above-average wages and works closely with them to bring out their best work.

SDP’s leadership promotes a culture of open communication, where every team member’s ideas are valued and considered. This inclusive approach builds a strong sense of camaraderie and trust. It’s also led to innovations that make projects safer and more cost-effective. 

His team knows that they will be recognized and rewarded for their contributions. Rapczynski promotes from within and encourages his staff to climb high. His COO, Derrick Tyler, started as an intern.  

Outside the SDP team, Rapczynski understands the importance of building solid relationships with local contractors and suppliers. By establishing long-term partnerships based on mutual respect and trust, he ensures that SDP’s projects have access to the highest quality materials and craftsmanship. 

A Legacy of Teamwork

Chris Rapczynski built Sleeping Dog Properties on a foundation of community. This has attracted some of the best contractors and laborers in the country to join his team. 

The strength of SDP’s leadership team has been a major reason for the company’s growth. Sleeping Dog Properties has expanded its service offerings outside Boston to New Hampshire, the Finger Lakes, and beyond. 

It has also earned numerous awards and recognitions for its excellence in contracting. SDP was recently honored in General Contractors Magazine as one of Cambridge, MA’s best general contracting firms. 

Chris Rapczynski plans to continue leading Sleeping Dog Properties with the same core values the company was founded on. Though he knows when it comes time to hang up his hard hat, his team will continue his integrity, innovation, and community-first approach legacy.