David is the Founder and Executive Chairman of Chess ICT, one of the UK's leading independent and trusted technology service providers, employing over 360 people across the UK and supporting over 30,000 business customers. David named the company after his two eldest children, Jess and Charlie, has received several accolades throughout his career, including Institute of Directors' Cheshire Director of the Year 2009 and seeing Chess top The Sunday Times 100 Best Companies to Work For list in 2018.

David was made Deputy Lieutenant of Cheshire in 2012 and received an Honorary Doctorate of Business from the University of Chester in May 2022

Stephen is an experienced telecoms & IT professional with over 35 years industry experience. After graduating from the University of Manchester, Stephen started his career with Lister and Co PLC working for them for 12 years, rising to the position of Head of IT.

Stephen then set up Hoodpoint Communications, specialising in providing ICT, Data and Voice communications and business phone systems. The business was sold to Chess in 2005.

Stephen stayed on at Chess, rising to the role of Group Managing Director in 2012. He became Chief Operating Officer in 2020 and runs the operational and commercial teams day-to-day. He is also closely involved in Chess Merger & Acquistions activity.

Richard is a prolific dealmaker with a record of more than 200 transactions (M&A, IPOs, JVs, including cross-border) as “corporate advisor” and, within industry, as Chairman and Director of private and listed companies.

With a highly entrepreneurial approach, Richard has been instrumental in formulating Chess’ strategy for growth in turnover from £5m to £150m over the past 10 years due to bank-supported acquisition activity. When not delivering strategic growth for Chess, Richard enjoys his passions for Modern British Art, skiing, tennis, and yoga. 

Jessica has a background in private equity and joined the acquisitions team in March 2023, and soon became Head of Acquisition for the Chess group in August 2024. She is inspired to make a great first impression, whilst focussed on maximising value with a smooth integration.   

We believe at Chess it is our growth that motivate our people, and Jessica’s ambition and determination for growth paired with her natural people skills is proving to be a successful combination as Chess continue their journey of growth, both organically and through acquisition. 

Jessica enjoys socialising with family and friends, she is also a frequent gym goer, however most of her free time is spent cheering at the side of sports pitches for her two sport loving sons.