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Jai Winston

Director, St. Paul
John S. and James L. Knight Foundation

Winston has been serving as a program director on the community and national initiatives team at Knight Foundation since 2016, where he leads the foundation’s initiatives in building a more vibrant, healthy, and equitable community of entrepreneurs, startups and small businesses in St. Paul, Minnesota with a multimillion-dollar active grant portfolio and more than $1 million in annual grant-making. In this role, Jai has prioritized investments that focus on accelerating economic growth and business development within the downtown area—with a strong emphasis on supporting entrepreneurs of color.

Previously, Winston was an associate of strategy and corporate development in the Office of the Chairman and Chief Executive Officer at Ariel Investments, a minority-owned money management firm in Chicago. At Ariel Investments, he focused on working with senior members of the firm and on other firm-wide strategic initiatives. In addition, he co-led several of the CEO’s special projects, including some of the firm’s national work on financial literacy and minority entrepreneurship.

Prior to joining Ariel Investments, Winston spent four years working at the nexus of politics, policy, and business. He worked on the 2013 Presidential Inaugural Committee with the White House Office of Intergovernmental Affairs. He served on the finance teams for President Barack Obama’s 2012 re-election campaign and the 2012 Democratic National Convention Host Committee.

Winston serves as vice chairman on the board for the Illinois Humanities Council and is also a trustee for Hamline University, serving as chair for the trusteeship committee. He is a member of the St. Paul Downtown Alliance board, and a member of the Community-First Public Safety Commission, appointed by Mayor Melvin Carter.

Winston earned a bachelor’s degree in political science from Howard University in Washington, D.C.

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