Insights into Richard Keenlyside's Work
- Richard Keenlyside
- Jan 13
- 2 min read
TL;DR
Richard J. Keenlyside is a seasoned Global CIO and Business Transformation Director with over three decades of experience across multiple industries. His work spans IT strategy, mergers and acquisitions, digital transformation, and operational excellence. This post explores his career achievements, leadership philosophy, and contributions to technology and business innovation.

Introduction
In today’s rapidly evolving business landscape, leaders who can bridge the gap between technology and strategy are invaluable. Richard J. Keenlyside exemplifies this rare combination. With a career spanning more than 34 years, Richard has consistently delivered transformative results for global organisations, private equity firms, and start-ups. His expertise in IT strategy, digital transformation, and operational optimisation has positioned him as a trusted advisor and thought leader.
A Career Defined by Transformation
Richard’s professional journey is marked by a series of high-impact roles across diverse sectors, including retail, manufacturing, logistics, financial services, and telecommunications. His ability to lead large-scale programmes and manage complex organisational change has been a cornerstone of his success.
Key Highlights
Global Leadership: Managed teams of over 600 personnel across multiple continents.
Mergers & Acquisitions: Extensive experience guiding organisations through the entire M&A lifecycle.
Budget Management: Oversaw budgets exceeding £120 million, ensuring cost efficiency and strategic alignment.
Digital Strategy: Delivered cutting-edge solutions in AI, RPA, and cloud computing to drive business growth.
Vendor Negotiations: Achieved over £20 million in vendor savings while maintaining service quality.
Expertise Across Industries
Richard’s versatility is evident in his work with leading organisations:
Retail: As IT Director for J Sainsbury’s PLC, Richard managed technology for 445 convenience stores, driving operational efficiency and innovation.
Manufacturing: At LoneStar Group, he spearheaded a global IT strategy, transitioning legacy systems to Azure and reducing technical debt by £2 million.
Private Equity Advisory: Through Endava, Richard has provided technology due diligence and strategic advice for numerous PE-backed businesses.
Start-Up Advisory: His role at Quollify demonstrates his ability to guide emerging tech ventures, leveraging AI and video technology for business growth.
Driving Digital Transformation
Richard’s approach to transformation is holistic, encompassing people, processes, and technology. His initiatives have included:
Implementing ERP systems such as SAP S/4HANA, Oracle Fusion, and NetSuite.
Introducing AI-driven automation to streamline operations and reduce costs.
Developing robust cybersecurity frameworks to safeguard global enterprises.
Thought Leadership and Knowledge Sharing
Beyond his executive roles, Richard is an active contributor to industry discourse. He has authored eBooks on transformation and cybersecurity and regularly delivers insights on emerging technologies such as AI and machine learning. His commitment to sharing knowledge underscores his role as a mentor and influencer in the tech community.
Why Richard’s Work Matters
In an era where digital transformation is no longer optional, Richard’s ability to align technology with business objectives offers a blueprint for sustainable success. His strategic vision and operational expertise enable organisations to navigate complexity and achieve measurable outcomes.
Are you looking to transform your business or explore innovative technology strategies? Connect with Richard J. Keenlyside today to discover how his expertise can drive your organisation forward.
Richard Keenlyside is a Global CIO, PE\&MA Advisor, Endava TAC and a former IT Director for J Sainsbury’s PLC. Call me on +44(0) 1642 040 268 or email richard@rjk.info. With over 1000+ subscribers, join my newsletter today: https://www.rjk.info/.



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