Jaclyn has a great deal of experience in both the private sector and the public sector. She previously served as a District Court judge in Taiwan, after which she worked as IBM's Taiwan General Counsel.

She founded Lee, Tsai & Partners in 1998 and specializes in technology law, M&A and investment matters.

In 2013, Jaclyn was appointed as the Minister without Portfolio in the Executive Yuan (Cabinet) and became one of the few female ministers in the government. During her term, she was responsible for a number of inter-ministry affairs, such as the reformation of laws related to virtual world development, e-commerce, the sharing economy, digital convergence, the startup environment, open data, and the maker movement.

Jaclyn returned to the law firm in 2016. She has been a committee member of both Taipei Smart City Committee and Taipei International Affairs Committee since 2017. Additionally, she serves as the Executive Director of Asia FinTech Alliance (AFA), the Honorary Chairwoman of both Taiwan FinTech Association (TFTA) and Taiwan Women on Boards Association (WOB.tw).