John Matthews

Managing Director

John is a managing director of AI research at Oaklins DeSilva+Phillips in New York and serves as Oaklins’ AI lead, being one of its experts on artificial intelligence matters. He advises founders, boards, private equity investors and corporate acquirors on sell-side, buy-side and strategic advisory assignments across artificial intelligence, enterprise software, SaaS, data and analytics, customer experience, martech, IT services, fintech, healthtech and digital media. Combining more than 15 years of investment banking and M&A advisory experience with deep expertise in AI, software and data-driven business models, John helps clients navigate transactions, growth strategies and value-creation opportunities in rapidly evolving technology markets. His work increasingly focuses not only on AI companies themselves, but also on the broader impact of AI on competitive positioning, business models, valuation methodologies, due diligence requirements, transaction structures and M&A activity across industries. Representative transactions include the sales of Fluidda to Banook Group, Epicenter (The People Platform) to Stagwell, Critical Mention to Onclusive, Helixa to Telmar, Admeta to WideOrbit, Ad-Juster to Innotech, Navita to Enghouse Systems and Vocada to Oracle. He has also contributed to several cross-border Oaklins transactions, including the sale of OBI4wan to Spotler Group and Grazper Technologies ApS to Yokogawa Electric Corporation.

Prior to joining Oaklins DeSilva+Phillips, John founded and led several technology research, advisory and consulting firms focused on artificial intelligence, enterprise software, fintech and customer relationship management. Among them was London-based INFACT Research, where he advised leading management consulting firms, private equity investors and technology companies, including McKinsey, Accenture, General Atlantic and 3i, on emerging technologies, market dynamics and investment opportunities. Earlier in his career, he was a senior industry analyst specializing in artificial intelligence and emerging technologies, and worked as an artificial intelligence and user experience (UX) software developer and designer. He also spent two years working on AI and UX initiatives in association with Xerox Palo Alto Research Center (PARC), one of the world’s most influential technology innovation centers. This combination of transaction advisory, technology operating experience, industry research and AI expertise provides John with a distinctive perspective on how artificial intelligence is reshaping industries, business models and investment priorities. He has a BSc in Computer Studies from Sheffield Hallam University in the United Kingdom.