Michael Ginsberg

As Executive Vice President at Chesapeake Contracting Group, Michael Ginsberg brings a rare blend of operational fluency, strategic foresight, and deep-rooted commitment to people and purpose. Having grown up with a front-row seat to the construction industry (his father, Bobby Ginsberg, founded the company), Michael’s journey has evolved from boots-on-the-ground learning into client focused leadership that helped shape the company’s growth across multiple market sectors.

“I grew up around construction, visited my dad’s projects as a kid and was always so impressed how he made big things happen,” Michael reflects. From a young age, he witnessed the full range of the business experience, from the thrill of winning competitive bids to the disappointment of near misses. That early exposure instilled a deep respect for both the craft and the culture of construction that combined hands-on experience, formal education at the University of Maryland, and steady advancement through key leadership roles within Chesapeake’s core markets.

Michael has played a key role in expanding Chesapeake’s presence across the Mid-Atlantic, particularly in the automotive and multi-family sectors. He led the delivery of 35 automotive facilities for nine major groups, beginning with a small body shop off Harford Road. His leadership helped position Chesapeake as the go-to partner for operationally complex dealership builds.

In multi-family housing, his leadership has resulted in the successful completion of over 1,500 apartment units, spanning both market-rate and affordable housing. He continues to serve on the board of CHAI (Comprehensive Housing Assistance, Inc.), bringing a broader civic lens to his work in neighborhood development and inclusive growth.

Yet for Michael, success is not just measured in square footage. It is about strategic impact. “We’re not just building projects. We’re building relationships that unlock new markets, attract repeat clients, and strengthen our reputation as a trusted partner.”

Michael’s management approach centers on perspective and collaboration. “My style is to see the project through our client’s perspective, trusting instincts that come from years of participating in the operations side of the business, collaboration and coaching within a team environment.” 

As Chesapeake’s scale and complexity have grown, Michael has embraced a culture of continuous improvement. He has played a pivotal role systematizing lessons learned, and advancing quality control metrics that reduce risk and enhance the client experience.

With geographic expansion and market diversification come new leadership demands. Michael has approached these challenges with clarity and resolve. “As we grow, one of the things I’m most focused on is protecting and evolving our culture,” he says. “Our people-first mindset is our differentiator.”

He is actively involved in shaping Chesapeake’s leadership development programs and change management initiatives. He recognizes that future success will require more than operational discipline. It will take adaptive leadership. This is especially important as the company embraces strategic shifts, integrates new technologies, and supports the development of future leaders.

When asked about Chesapeake’s core values, Michael gravitates toward Relationships. “Everything comes down to people and shared experiences. We’re in the people building business. These are the things that tie us together and I’m always striving to create excellent experiences.”