Following college, he and his brother Jesse Kirkland began training in an attempt to qualify for the 2012 Olympic Games in London in the 49er event.

During the 2012 49er World Championship in Croatia, the brothers finished in the Gold fleet and thereby qualified to represent Bermuda in the 2012 Olympics.

He attended college in the United States at Tufts University in Massachusetts, and sailed while a student.

They advanced to the gold fleet after the preliminary qualifying races and later became the first team to secure one of the five remaining Olympic qualifying places that remained at the time after finishing in eighth place out of seventy-four in the final standings.

[3] After their success in Croatia, they likewise left early for Weymouth, England, in order to get used to local sailing conditions prior to the start of the Olympic Games.