A native Staten Islander, Caroline is a graduate of Staten Island Academy and holds a B.A. from Dartmouth College. Caroline and her husband Tim are the proud parents of two SIA graduates, Timothy Jr, Class of 2012, and Alice, Class of 2014.
Caroline is Chief Executive Officer of Advance Local and is also Publisher of the Staten Island Advance and its affiliated website, silive.com.
Caroline began her career at the company as a college intern reporter at the Staten Island Advance. Upon graduation, she became an Executive in Training at the New Orleans Times-Picayune and then the Patriot-News in Harrisburg, PA, before returning to the Advance in 1999 as General Manager, working closely with her father, longtime Publisher, Richard E. Diamond. In April of 2004, shortly after her father’s death, she was named Publisher of Advance. Caroline was named President of Advance Local in January 2018 and CEO in April 2020.
Advance Local is a leading U.S. digital media and marketing company, delivering award-winning local journalism and innovative business solutions to communities nationwide. Advance Local, which today operates in markets across the country including Oregon, Ohio, Michigan and Massachusetts, got its start more than 100 years ago when Caroline’s great uncle SI Newhouse purchased the Staten Island Advance in 1922. Through massive technological change, the company has evolved for today’s digital age, while remaining true to its origins in its present-day mission. The company’s mission statement sums up the heart of Advance Local, which is, “To Strengthen and Empower the Communities we serve.” Through its affiliated newsrooms Advance Local has earned multiple awards in recent years, reflecting its commitment to impactful journalism. Most recently in 2023, the AL.com team was awarded Pulitzer Prize awards for Local Reporting and Commentary. Recognized for an investigation into predatory policing in Brookside, Alabama, the local reporting led to the removal of police officers, changes in state law, dismissal of court cases, and the release of jailed individuals.
The Staten Island Advance/SILive.com has consistently earned recognition for its impactful journalism, securing numerous awards across prestigious contests in recent years. In 2024, the newsroom won 10 honors from the New York News Publishers Association, New York Press Club, and New York Newswomen’s Club. These honors celebrated outstanding work in categories such as feature writing, crime reporting, investigative journalism, photography, and community service. Notably, the “Rebuilding Sandy Ground” series— highlighting the historic Black settlement on Staten Island’s South Shore—garnered multiple awards for its in-depth reporting and compelling visuals. In previous years, the Advance also received accolades for coverage of major events like Hurricane Ida and for impactful series such as “Pride and the Parade,” which earned the Distinguished Community Service Award. These achievements underscore the publication’s commitment to serving its community through high-quality, locally focused journalism.
Caroline serves as a board member of the Richmond County Savings Foundation. She previously served as an Elective Trustee of The Metropolitan Museum of Art, on the Staten Island Academy board (former President, 2011-2015), as Chair of the Board of the Hopkins Center for the Arts at Dartmouth College, on the Board of directors of the Alliance for Audited Media, on the Board of Directors for Mutual Insurance Company and on the board of the Newspaper Association of America
Caroline’s leadership has been recognized through numerous awards and honors that reflect her deep commitment to journalism, community service, and civic engagement:
- In 2025, Caroline and her mother Alice Diamond received honors from the JCC’s Women Front and Center for their dedication to female empowerment and community impact.
- In 2023, Caroline and her husband Tim were honored by the Wagner College DaVinci Society as Honorable Ralph Lamberti Renaissance Award honorees for the significant contributions to Staten Island’s cultural and civic life.
- In 2018, Caroline received College of Staten Island’s Presidential Medal for her outstanding leadership and service to the Staten Island community.
- In 2016, Caroline was honored by the New York Harbor Conservancy in Federal Hall in Lower Manhattan for her efforts to improve Staten Island.
In addition to these accolades, Caroline has continued to honor a tradition started by her father in 1962 with the Women of Achievement Awards. This program celebrates women who make significant contributions to the Staten Island community. This program has evolved to encourage volunteerism and community partnerships by mentoring and granting scholarships to students that display volunteerism traits.