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After law school, Jackson served as a law clerk to Judge Patti B. Saris of the U.S. District Court for the District of Massachusetts from 1996 to 1997, then to Judge Bruce M. Selya of the U.S. Court of Appeals for the First Circuit from 1997 to 1998. She spent a year in private practice at the Washington, D.C. law firm Miller Cassidy Larroca & Lewin (now part of Baker Botts), then clerked for Justice Stephen Breyer of the U.S. Supreme Court from 1999 to 2000.^[1][2]

Jackson worked in private legal practice from 2000 to 2003.^[3] From 2003 to 2005, she served as an assistant special counsel to the United States Sentencing Commission.^[4] From 2005 to 2007, Jackson was an assistant federal public defender in Washington, D.C., where she handled cases before U.S. Court of Appeals for the D.C. Circuit.^[5] A Washington Post review of cases Jackson handled during her time as a public defender showed that "she won uncommon victories against the government that shortened or erased lengthy prison terms".^[6] From 2007 to 2010, Jackson was an appellate specialist at Morrison & Foerster.^[3][2]

U.S. Sentencing Commission

On July 23, 2009, Barack Obama nominated Jackson to become vice chair of the United States Sentencing Commission.^[7] The U.S. Senate confirmed Jackson by unanimous consent on February 11, 2010. She succeeded Michael E. Horowitz, who had served from 2003 until 2009. Jackson served on the Sentencing Commission until 2014.^[8][2] During her time on the Commission, it retroactively amended the Sentencing Guidelines to reduce the guideline range for crack cocaine offenses,^[9] and enacted the "drugs minus two" amendment, which implemented a two offense-level reduction for drug crimes.^[10]