Sherwood-Randall served as deputy assistant secretary of defense for Russia, Ukraine, and Eurasia during the first Clinton administration (1994-96.) In this role, she developed and implemented regional security policy toward all the newly independent states of the former Soviet Union, including Russia, Ukraine, the Caucasus, and Central Asia, and established defense and military relationships with each of these states. She was instrumental in extending NATO's Partnership for Peace program across Eurasia and in building the foundation for cooperation between Russia and NATO in the joint peacekeeping operation in Bosnia. She has also served as a consultant to the Office of the Secretary of Defense and as a member of the Pentagon's Regional Centers' Board of Visitors, and as an adviser to the Lawrence Livermore National Laboratory on its nonproliferation and arms-control initiatives in the former Soviet Union.
Prior to her government service, Sherwood-Randall served as cofounder and associate director of Harvard University's Strengthening Democratic Institutions Project. She previously served as chief foreign affairs and defense policy adviser to Senator Joseph R. Biden, Jr. and as a guest scholar in foreign policy studies at the Brookings Institution. She has also worked as a journalist and as editorial page editor of the Santa Fe New Mexican.
Sherwood-Randall serves on the board of governors of the Commonwealth Club of California. She is a member of the Aspen Strategy Group, the National Security Advisory Group to the U.S. House and Senate Democratic leadership, the Council on Foreign Relations, and the International Institute for Strategic Studies. In 2006 she wrote "The Case for Alliances," in Joint Force Quarterly, and "Alliances and American National Security," published by the U.S. Army War College Strategic Studies Institute. She also coauthored "The Case for Discriminate Force," published in Survival in 2002. She is the author of Allies in Crisis: Meeting Global Challenges to Western Security, published by Yale University Press in 1990.
Sherwood-Randall received her bachelor's degree from Harvard College, magna cum laude, and a D.Phil. in international relations from Oxford University, where she was a Rhodes Scholar (California and Balliol, 1981.)