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Gillian Caldwell graduated magna cum laude from Harvard University in 1988 before going on to study public interest law at Georgetown University (1989–1992). From 1995-1997, she served as the co-director of the Global Survival Network, where with her colleague Steven Galster she organized a two-year undercover investigation into Russian Mafia involvement in trafficking women for forced prostitution. Her work was cited in a book by David Bales titled Disposable People: New Slavery in the Global Economy. Caldwell produced and directed Bought & Sold: An Investigative Documentary into the Trade in Women, which received media coverage in the United States and abroad, including specials on ABC Primetime Live, CNN, and BBC.

Caldwell was the campaign director of 1Sky from 2007-2010. 1sky grew to become one of the largest collaborative campaigns on climate change in the United States. 1Sky's goal was to create five million green jobs through an energy efficiency and conservation wave, to enact a federal cap on global warming pollution with steep reductions in carbon pollution, and to transition the United States off of coal and onto renewable energy sources. 1Sky completed a planned merger with 350.org after Caldwell's departure.

Caldwell was the president of Gillian Caldwell Consulting LLC from late 2010 to July 2015, serving as an executive coach, strategic planner, retreat facilitator, and organizational development consultant to NGOs, as well as foundations, socially responsible corporations, films, and the White House. In 2013, she was the producer, along with Tia Lessin and Carl Deal, of Citizen Koch, which premiered at the Sundance Film Festival. Citizen Koch was the subject of a Jane Mayer article in The New Yorker and extensive press nationwide.

Caldwell served as executive director at Witness, an organization co-founded by musician Peter Gabriel to empower human rights advocates to use video to create change. During her time there Caldwell co-authored Video For Change: A Guide to Advocacy and Activism and produced and directed videos on human rights challenges worldwide, including Outlawed: Extraordinary Rendition, Torture and Disappearances in the War on Terror, Operation Fine Girl: The Use of Rape as a Weapon of War in Sierra Leone and Behind the Labels: Garment Workers on US Saipan.

Caldwell was appointed as executive director of Global Witness in July 2015. The organization has offices in London, Washington, D.C. and China. Her work was based in the London office until 2019, when she relocated to the Washington DC area to restart her consulting practice, Gillian Caldwell Consulting LLC. In 2021, she was brought on to the USAID as their new Climate Change Coordinator and Deputy Assistant Administrator.