Cherry began her career as a VISTA volunteer in Tennessee. She spent the next several years as a field examiner in the New England region of the National Labor Relations Board.[1]
After earning a J.D. from Northeastern University School of Law, she joined the law firm of Hale and Dorr (now WilmerHale). For eight years, she focused on commercial real-estate finance and development, for which she was named a partner.[2]: 114
In 1992, Cherry joined the Plymouth Rock family of insurance companies, where she served as a vice president and counsel of SRB, an investment-management subsidiary of Plymouth Rock Assurance.[1]
In 1997, she became the CEO of BlueHub Capital,[3] which she co-founded in 1984.[4]
BlueHub Capital
Under Cherry's tenure, BlueHub Capital (formerly Boston Community Capital[5]) has invested more than $2 billion in low-income communities.[6]
Of note is BlueHub's foreclosure-prevention program, SUN,[7][8] which Ben Bernanke, then the chairman of the Federal Reserve, cited as “innovative.”[9]
Cherry is a former or present member of several privately held company boards, including include Zipcar,[citation needed] Pilgrim Insurance,[14] Acelero Learning,[15] Selectech,[16] and WegoWise,.[17]
Cherry is a prominent LGBTQ activist. She has served on the boards of directors and advisory boards of various groups, including GLBTQ Legal Advocates & Defenders (GLAD),[4]MassEquality during the organization's successful campaign to legalize same-sex marriage in Massachusetts,[23] the political action committee LPAC,[24] and the Boston Foundation’s Equality Fund.[25] She also co-chaired GLAD’s capital campaign, One Justice Fund,[26]
which raised $1.7 million.[27]
Education
Cherry is a 1975 graduate of Wellesley College, where she studied political science and from which she received the 2017 Alumnae Achievement Award.[28] She is also a 1983 graduate of Northeastern University School of Law,[29] where she delivered the student commencement address.[30]
Awards
Cherry has received many awards throughout her career.
In 2014, Fenway Health gave her the Dr. Susan M. Love Award, which celebrates a woman and/or organization that has made a significant contribution to the field of women’s health.[36]
In 2021, BlueHub Capital, under Cherry's leadership, was named one of the Top 100 Women Led Businesses in Massachusetts by The Boston Globe and The Commonwealth Institute for the eighth consecutive year.[37]
Media
Cherry is a frequent commentator on current events. Her opinion articles have appeared in publications including the New York Times,[38] CNBC,[39] the Los Angeles Times,[40] the Philadelphia Inquirer,[41] and HuffPost.[42] She has also appeared on TV and radio shows such as the PBS NewsHour[43] and Making Money with Charles Payne.[44]