Gifford started in Democratic politics by working on John Kerry's 2004 presidential campaign, and subsequently started his own consulting business and advised numerous Democratic officials and advocated for progressive causes across the country. He first met then-Senator Barack Obama in January 2007, at a party hosted by Senator Ted Kennedy. Prior to the meeting, Gifford had been offered a job on Hillary Clinton's 2008 presidential campaign, but he declined and instead accepted the same job for Obama's campaign. After Obama took office, he served as Finance Director for the Democratic National Committee in Washington, D.C. before moving to Chicago as a senior staff member of President Obama's 2012 re-election campaign. As National Finance Director for the re-election campaign, he was ultimately responsible for the record-setting billion-dollar budget.
U.S. Ambassador to Denmark (2013-2017)
On August 1, 2013, Gifford's nomination from President Obama to be the next United States Ambassador to the Kingdom of Denmark was confirmed by the United States Senate. He was sworn into the role on August 15, 2013, and presented his credentials to the Queen of Denmark on September 13, 2013. In his capacity as the Ambassador, he helped modernize the transatlantic relationship through youth engagement and institution-building, among other bilateral and global issues. He outlined a diplomatic strategy that prioritized non-traditional audiences and people-to-people relationships. As part of a never-before-seen public diplomacy strategy, he was the subject of the documentary series I am the Ambassador. The documentary TV series about his life as an ambassador ran for two seasons, winning the Big Character award at the 2015 TV-Prisen award-show. As Ambassador, he traveled to Greenland for bilateral meetings on climate change, promoted counter-extremism initiatives and Danish–American trade, and worked to maintain Danish military support in Iraq and Afghanistan. In 2016, he accompanied U.S. Secretary of TransportationAnthony Foxx and several American mayors on a bike ride around Copenhagen to showcase its success as a "cyclist-friendly city." Gifford was an integral part of bringing the American art form of Long Form Improvisation to Denmark. In September 2016, he was in the opening show at the first improv theatre in Denmark, , and said, "No matter what you are doing, you always have to allow time to laugh, smile and have fun. And creating that balance is incredibly important." Gifford served as an honorary board member of the American-Danish Business Council. On January 16, 2017, Gifford was awarded the Grand Cross of the Order of the Dannebrog by Her Majesty Queen Margrethe II of Denmark for his "meritorious service to the Kingdom of Denmark."
Gifford is gay, and commentators from GQ, Huffington Post, and L.A. Weekly referred to him as Barack Obama's informal "ambassador to the gay community." He is a Federal Club Member of the Human Rights Campaign and a Partner in Conservation for the World Wildlife Fund. Gifford married his husband, Dr. Stephen DeVincent, a veterinarian, on October 10, 2015 in a ceremony at Copenhagen City Hall in Copenhagen, Denmark. They live in Concord, Massachusetts. In 2016, Gifford co-wrote a cookbook with his husband, called The Ambassador's Kitchen. Gifford is the son of Charles K. Gifford, a banker who is the chairman emeritus of Bank of America.