Our Team

Josh Zakim
Founder & Principal

Josh Zakim is an attorney and former Boston City Councilor.

After six productive years on the Boston City Council, Josh chose not to seek re-election, leaving the Council in January 2020. 

As a Boston City Councilor Josh has been intimately involved in all aspects of Boston’s government, but has also had the opportunity to work regionally and across the Commonwealth of Massachusetts. On the Council, Josh chaired the Committee on Housing & Community Development; the Committee on Civil Rights; and the Special Committee on Transportation, Infrastructure, Planning, & Investment. In this capacity Josh convened policymakers and researchers to find solutions, and in many cases enacted legislation to address important issues including housing, transportation, small business growth, civil rights, and fiscal policy. Josh led by partnering with other municipalities, state government, colleges and universities, and leaders in the private sector.

In 2018 Josh ran for Massachusetts Secretary of State on a platform of improving voter access, civic engagement, and transparency. During this statewide campaign Josh earned the endorsement of the Massachusetts Democratic Party and dozens of elected officials, developing and maintaining strong relationships with mayors, legislators, and political activists across the state. 

During his time on the Boston City Council, Josh developed close working relationships with elected and appointed government officials across Massachusetts at the city, state, and federal level. Josh has seen up close how public policy decisions are made and implemented. As a former legislator himself, Josh knows what motivates public policy decision makers and how a case should be made to achieve a particular outcome. He has a long record of success in persuading fellow legislators, state, and executive officials to endorse and support major policy changes.

Caroline Humphrey Clifford
Vice President & Counsel

Caroline Humphrey Clifford is an attorney and currently serves as Vice-President & Counsel at Zakim Strategies. In this role she leads our internal investigations, criminal justice, and security practice. A current member of the Massachusetts Bar, Caroline provides legal services and has expertise in developing litigation strategy. She also works with real estate, cannabis, and other clients in navigating the sometimes complex permitting and community processes in the City of Boston and throughout the state.  

Prior to joining Zakim Strategies, Caroline served as an Assistant District Attorney in the Suffolk County District Attorney’s Office for nearly six years, where she prosecuted hundreds of cases, including numerous trials in both the District and Superior Courts. While working in the Major Felony Bureau, she tried some of the most complex criminal cases in the Commonwealth and secured multiple indictments before the grand jury. During her time as a prosecutor, Caroline developed a reputation for tireless investigatory work and tenacity in all phases of litigation – from initial indictment through trial and appeal.

Born and raised in Boston, Caroline has an intimate knowledge of the communities that make up the city as well as long-standing relationships in both the public and private sectors. Outside of work, she enjoys giving back as a member of the Board for the Bridge Center, a non-profit providing year-round therapeutic recreational programs for children with disabilities, and the Young Partners Council for the Boston Ballet.

Caroline earned a Bachelor of Arts from Georgetown University where she studied Philosophy and English.  She received her law degree from Suffolk University Law School.