[1] Penn was the first woman to be appointed Deputy Governor, and the first British Virgin Islander to serve as Attorney General.
She served briefly as the acting Governor of the British Virgin Islands during 2006 in the gap between Tom Macan leaving office and David Pearey taking up his appointment.
[2] She was elected to office, defeating the incumbent Lloyd Black, and she was appointed the Minister of Health and Welfare, and as the Deputy Premier of the British Virgin Islands.
However, in the General Election held on 7 November 2011 she lost her 8th district seat to Marlon Penn.
[3] There had been considerable speculation after the 2007 that when the then Premier of the British Virgin Islands, Ralph T. O'Neal retired, Penn would be named as his successor as leader of the Virgin Islands Party, and would thereby become the first female Premier in the Territory.