Sheryl Goldstein is the Founder of Pluck, which advises and guides organizations to create and implement lasting change. In this role, Sheryl works with businesses and non-profits to assess challenges and design solutions, governments to improve their operations, and philanthropists to maximize the impact of their investments.
Sheryl has over 30 years of diverse operational experience in the corporate, non-profit, government, and philanthropic sectors, having served in numerous senior roles. During her career, she has built a reputation for operational excellence, innovative strategic thinking and problem-solving, fairness and honesty. She is known for her ability to advise key leaders and executives, supporting them to be successful and execute on their missions. Sheryl is a quick study, grasping complex concepts quickly and using research and data to inform the advice she gives, decisions she makes and problems she solves. Her resume reflects her core desire to motivate, mentor, and fundamentally improve the world around her.
Prior to launching Pluck, Sheryl was the Deputy Chief of Staff for Operations for Baltimore City Mayor Bernard “Jack” Young. In that role, she oversaw Baltimore’s core infrastructure and human services agencies, managing and mentoring ten agency heads and providing daily advice to Mayor Young and his Chief of Staff. Notably, she led Baltimore’s recovery efforts after a ransomware attack and was responsible for overseeing the City’s COVID-19 pandemic response.
Sheryl worked in philanthropy for six years, most recently as the Vice President of the Abell Foundation. As Vice President, she served on the board of directors as an officer, advised the President, reviewed grant and direct investment recommendations, and oversaw day-to-day operations. Before joining Abell, she was the Managing Director of Programs and Grants at the Harry and Jeanette Weinberg Foundation. In that role, Sheryl managed program staff, advised the President and worked extensively with the board. While at Weinberg, she developed a new strategic direction for the foundation’s education grantmaking, presented it to the board for approval and built a $25 million grant portfolio to support it. She also led the creation of Baltimore’s Summer Funding Collaborative that brings together over a dozen funders to streamline grantmaking and support to high-quality summer programs serving children and youth from low-income backgrounds in Baltimore City. In both positions, Sheryl identified and explored new investment opportunities, conducted extensive due diligence on grant applications and potential grantees, and reviewed financial statements and budgets.
Between 2007 and 2012, Sheryl served as the Director of the Mayor’s Office on Criminal Justice in Baltimore where she was responsible for developing, coordinating and implementing Baltimore City’s criminal and juvenile justice strategies. She was an advisor to the Mayor and former Police Commissioner Frederick Bealefeld and managed $60 million in grant funds. During her tenure, she played an instrumental role in designing and implementing Baltimore’s gun violence reduction strategy and reforming the criminal justice system’s response to sexual assaults. She also reshaped Baltimore’s crime camera program, making it more effective in reducing crime and decreasing the program’s costs by $1 million per year.
Sheryl began her professional career as an attorney and litigated criminal, civil and employment cases in state and federal courts for seven years. She received her B.A. at the University of Michigan and earned her Juris Doctorate from Georgetown University Law Center. She is admitted to the Maryland, New York and Michigan Bars. Sheryl currently serves on the Baltimore Equitable Insurance and Baltimore Equitable Insurance Foundation boards.