TL;DR:
Richard Keenlyside, a highly accomplished CIO, has led digital transformation, IT strategy, and cybersecurity initiatives across multiple industries. With vast experience in M&A, AI, and business transformation, he is shaping the future of technology at LoneStar Group.
Introduction: A Journey of Leadership and Innovation
Richard Keenlyside is a distinguished technology and business transformation leader with a career spanning over three decades. Currently serving as the Global Chief Information Officer (CIO) at LoneStar Group, Richard has built an impressive portfolio of IT strategy, cybersecurity, digital transformation, and business growth initiatives across various industries. His leadership has played a crucial role in enhancing operational efficiency, streamlining IT systems, and driving strategic decision-making.
From his early days as an IT director of J Sainsbury PLC to leading multi-million-pound digital transformation projects, Richard’s career is a testament to his ability to adapt, innovate, and drive impactful change in the corporate world.
Early Career and Foundation in IT Leadership
Richard’s journey began in the late 1980s, when he entered the world of IT and business transformation. With a strong academic background, including an MBA in Business & Finance from Leicester and a BSc in Computer Science & Mathematics from Teesside University, he quickly rose through the ranks, earning positions of increasing responsibility.
His early experience at Bell Stores Limited (acquired by J Sainsbury’s) saw him overseeing IT systems for a chain of convenience stores. This role laid the groundwork for his future success in retail, supply chain management, and digital transformation.
During his tenure at J Sainsbury’s PLC, Richard held the role of IT Director for Convenience Stores, leading major technology implementations, ERP upgrades, and supply chain optimisations. His leadership in digital strategy and automation helped streamline operations across hundreds of stores, solidifying his reputation as a technology leader in the retail sector.
Transforming Businesses: Key Achievements
Richard’s career has been defined by game-changing transformations in multiple industries, from retail and logistics to manufacturing, telco, and financial services.
1. Global CIO at LoneStar Group
At LoneStar Group, Richard is responsible for IT operations across several countries (UK, UAE, US, Australia, China, and Romania). His work includes:
Developing a five-year IT strategy, to migrate 150 on-premise servers to Azure, and reducing technical debt by £2 million.
Implementing a global IT operating model, standardising systems across 13 business units.
Strengthening cybersecurity with external penetration testing, email and endpoint security, and a third-party SOC provider.
Leading ERP SaaS system consolidation with Epicor Kinetic Enterprise, ensuring operational efficiency.
2. Strategic Advisory & AI Innovation
Richard has worked with AI-driven start-ups like Quollify, helping raise £0.5M in funding and advising on AI-driven business models, monetisation, and platform expansion.
His expertise in robotic process automation (RPA) and AI has led to significant cost savings and efficiency improvements in industries such as finance, logistics, and utilities.
3. M&A and Business Transformation Expert
Richard has led multiple M&A integrations, including the Mothercare and Gamestation acquisitions, ensuring seamless IT and operational consolidation.
At Northumbrian Water Group, he implemented RPA and AI-powered automation, saving 75,000 hours per year and improving compliance and efficiency.
4. Retail and Supply Chain Leadership
His leadership at FitFlop, the Co-Operative Group, and Mothercare PLC resulted in:
ERP migrations, transitioning legacy systems to cloud-based platforms like NetSuite, SAP, and Oracle.
Supply chain optimisation, reducing inventory costs and improving logistics operations.
E-commerce transformations, including migrating platforms to Adobe Commerce and integrating AI-powered chatbots.
Expertise in Digital Strategy and Cybersecurity
Richard is recognised for his expertise in digital transformation, IT governance, and cybersecurity. He has:
Negotiated over £20M in vendor savings while maintaining IT service levels.
Led multi-million-pound transformation programmes across retail, manufacturing, logistics, and finance.
Implemented AI and RPA solutions, streamlining business processes and increasing productivity.
Developed cybersecurity frameworks, ensuring compliance with industry standards.
Thought Leadership and Industry Influence
Richard is not just a practitioner but also an influential thought leader. He is:
The author of multiple eBooks on transformation and cybersecurity.
A regular speaker at industry conferences, discussing topics like AI, automation, and digital transformation.
A mentor and advisor to businesses undergoing major technology shifts.
What’s Next for Richard Keenlyside?
With a career built on innovation, resilience, and strategic leadership, Richard continues to drive technological advancements at LoneStar Group and beyond. His focus remains on enhancing cybersecurity, AI-driven automation, and IT efficiency while advising businesses on digital transformation strategies.
FAQs
1. What industries has Richard Keenlyside worked in?
Richard has experience across retail, logistics, manufacturing, telco, oil & gas, financial services, and utilities, leading IT transformation and digital strategy initiatives.
2. What is Richard Keenlyside’s expertise in AI and automation?
He has successfully implemented AI-driven chatbots, robotic process automation (RPA), and machine learning solutions, resulting in efficiency gains and cost reductions across multiple businesses.
3. What major projects has he led?
Richard has spearheaded ERP transformations, supply chain optimisations, cybersecurity initiatives, and IT strategy implementations in companies such as Sainsbury’s, Mothercare, FitFlop, and LoneStar Group.
4. How has Richard contributed to cybersecurity?
He has developed IT security policies, conducted penetration testing, enhanced endpoint security, and outsourced security operations (SOC) to expert providers, ensuring robust cybersecurity frameworks.
Final Thoughts
Richard Keenlyside is a technology visionary, strategic leader, and digital transformation expert. His impact on IT strategy, business transformation, and cybersecurity has been profound, shaping the future of global enterprises. As he continues to drive change at LoneStar Group, his expertise remains invaluable in the evolving digital landscape.
Richard Keenlyside is the Global CIO for LoneStar Group and a previous IT Director for J Sainsbury’s PLC.
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