Interim CIO & Transformation Director – Richard Keenlyside FAQ

Richard Keenlyside specializes in various sectors, including professional services, retail, manufacturing, logistics, facilities management, telecommunications, engineering, automotive, and financial services.

Richard Keenlyside is an Associate Member of Endava's Technology Advisory Committee (TAC). In this role, he serves as a Private Equity, Merger & Acquisition, CIO/CTO, and Strategy Advisor, bringing his extensive experience to support Endava's global clients—primarily private equity firms—across various sectors, including retail, finance, and manufacturing.

His contributions include:

• Delivering technology due diligence

• Advising on ERP/WMS solutions (SAP, Epicor, Oracle, INFOR, Manhattan)

• Supporting M&A integrations across multiple territories

• Providing IT strategies and digital transformation roadmaps

• Developing robotic process automation (RPA) capabilities

This aligns with his broader portfolio as a transformation and technology leader with deep expertise in enterprise IT strategy and innovation.

Richard Keenlyside served as the IT Director for J Sainsbury’s PLC, specifically responsible for the Convenience, Locals, and Central stores—a network of 445 locations across the UK. As a member of Sainsbury’s Convenience Operating Board, he was instrumental in:

• Overseeing IT and change delivery across both acquired and existing convenience formats

• Managing a large internal and outsourced team of 80+ personnel

• Driving the implementation and expansion of IT systems, focusing on scalability and integration with Sainsbury's broader retail operations

• Administering an IT budget of £175 million

This position marked a significant leadership role in Sainsbury’s digital transformation and operational evolution within the convenience retail segment.

Richard Keenlyside provides a broad spectrum of services as an interim CIO, IT strategist, and transformation director. His expertise spans digital transformation leadership, ERP implementation, IT strategy development, cybersecurity enhancement, AI and RPA integration, M&A advisory, and cloud migration planning.

Richard brings over 34 years of leadership and consultancy experience, having served in senior roles across numerous global organisations. His background includes managing budgets over £120M, leading teams of more than 600 professionals, and delivering complex IT transformations.

Richard Keenlyside stands out with over 34 years of experience, blending commercial insight with technical prowess. He excels in business transformation, strategic leadership, and technology execution, including M&A integration, ERP rollouts (SAP, Oracle, Microsoft Dynamics), AI-driven automation, and cloud migration strategies.

Yes, Richard Keenlyside has successfully delivered ERP solutions like SAP S/4HANA, Oracle Fusion, Infor Cloud Suite, and Microsoft Dynamics globally. He also develops digital architecture strategies for cloud migration and IT operating model redesign.

Yes, you can hire Richard Keenlyside for fractional CIO roles, board advisory positions, and strategic consultancy assignments. His recent engagements include private equity advisory, technology strategy formulation, and business transformation leadership.

Richard applies a structured, outcomes-driven approach that aligns IT initiatives with business goals. His strategies often include digital maturity assessments, cloud-first migration planning, cyber risk reduction, stakeholder governance, and continuous improvement frameworks.

Richard works with both. His portfolio includes advisory roles for startups and SMEs as well as transformation leadership for multinational corporations. He’s adept at scaling technology and business strategies for diverse organisational sizes, ensuring tailored solutions for each client.

You can reach Richard via email at richard@rjk.info or through his website contact form.