From 2012 to 2014 he worked at 10 Downing Street as Private Secretary to the Prime Minister, David Cameron, after which he spent a year studying at the Royal College of Defence Studies, an institution which grooms public servants who "have the potential to reach the highest ranks".

[6][7] Shortly after being sworn into office as Governor, the British Virgin Islands was struck by Hurricane Irma.

Jaspert declared a state of emergency 16 days after being sworn in, thus becoming the first ever Governor of the British Virgin Islands to exercise that power under the Constitution.

[8] Shortly before demitting office Jaspert launched a corruption inquiry in the Territory,[9] appointing Sir Gary Hickinbottom commissioner.

Sir Gary's report concluded that governance in the Territory had been "appallingly bad", and that it was "highly likely" that serious dishonesty had taken place.