Having been the principal Costs Draftsman for the Solicitors Indemnity Fund before and after they entered into run-off in 2000, Simon has worked for most of the insurance market that followed the Solicitors Indemnity Fund including (but not limited to) AIG Europe, Zurich Insurance, Travelers, QBE Insurance, AXA XL, Royal Sun Alliance, Hiscox Insurance, AXIS, Sompo International, AMTrust & MS Amlin.

In the course of working with the Solicitors Indemnity Fund Simon had involvement in three sets of case managed litigation where the Solicitors Indemnity Fund were faced with seven figure claims for costs from respectively, The Bristol & West Building Society, The Nationwide Building Society and Paragon Finance PLC. Since then Simon has also acted for 5 Insurers in relation to the TAG & CLE litigation and other insurers in relation to claims for costs arising out of the PPP investors' litigation and property transactions in the North of England.

In 2003/04 Simon advised the Claimant's Solicitors in litigation involving a claim for negligence against a well-known international auction house arising from the under-valuation of a painting later found to be worth in excess of £7 million. The Claimant's claim for costs amounted to in excess of £3.2 million. The monetary value of the Claimant's claim for a success fee of 100% was the largest claim proceeding in the Senior Courts Costs Office at that time.

In the course of his career Simon has attended numerous detailed assessment hearings and at CCMCs. Simon has had involvement in a number of important and reported cases involving the interpretation of the indemnity principle, conduct, in-house legal fees and the level of success fees. He has also acted as an expert witness and has had articles published online.

Simon was also very pleased to be asked to participate in the initial private consultation meetings with Lord Justice Jackson in early 2009 at the Royal Courts of Justice involving the Third Party Funding Market and the After the Event Insurance Market. The private and public consultations culminated in the Ministry of Justice moving forward with a radical overhaul of the costs system in England & Wales in 2013. As a result, this has led to a change to Simon's more familiar workload and has seen him move towards developing other markets, such as advising D&O insurers in relation to claims for costs arising out of civil and criminal investigations overseas, the USA in particular. Simon has seen his client base grow in recent years in relation to media work having acted for many of the national newspapers & media organisations in costs proceedings arising out of privacy, defamation and libel claims, including the detailed assessment proceedings in Duchess of Sussex -v- Associated Newspapers, Lord Sheikh -v- Associated Newspapers, Alaedeen Sicri -v- Associated Newspapers, Various Claimants -v- Channel 5, Bruno Lachaux -v- The Independent and The Evening Standard & Patsi Kensit -v- MGN Ltd to name but a few.