Leigh Hamilton developed her business and entrepreneurship skills by founding an Irish online recruitment business in 1998 which she grew and later sold to a large international recruitment company in 2003. She was called to the Bar of Ireland in 2002 and developed a practice as a trial lawyer specialising in clinical negligence cases, with a reputation for advocacy and negotiation. In 2015 she joined the family business, Piper Systems and took up the position of CEO in 2019.