Simon has practised as a barrister in Sydney since 2010 and was appointed Senior Counsel in 2024. He had previously worked in New York, taught at the University of Sydney Law School, and been an associate at the High Court of Australia.

Simon’s practice includes commercial and corporate law, equity, insurance, professional indemnity, public law and trade practices. He has appeared in representative proceedings (for applicants and respondents), commissions of inquiry (as counsel assisting ICAC, and for persons and institutions affected), and trials and appeals in federal, state and territory courts.

Simon is ranked as a ‘2024 Silk’ in The Legal500 Asia-Pacific Guide for Commercial Disputes: ‘Simon is an excellent barrister. He is academically rigorous, commercially pragmatic, prompt in the turn around of work, and collaborative in his approach’. Best Lawyers in Australia also recognises Simon in the area of Litigation (9th ed, 2017 to 17th ed, 2025).

Simon is a member of the Executive of the Law Council of Australia's Federal Dispute Resolution Section, and since 2019, has served on a Professional Conduct Committee of the NSW Bar Association.  He was also a volunteer Director of the Marrickville Legal Centre from 2016 to 2021.