Question 1

What industries do I specialize in?

Accepted Answer

I specialize in various sectors, including professional services, retail, manufacturing, logistics, facilities management, telecommunications, engineering, automotive, and financial services.

Question 2

Private Equity, Merger Acquisition, CIO/CTO & Strategy Advisor at Endava

Accepted Answer

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.

Question 3

Richard Keenlyside - former IT Director for J Sainsbury’s PLC

Accepted Answer

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.

Question 4

How can I benefit your business?

Accepted Answer

I offer a wide range of services as an interim CIO, IT strategist, and transformation director. My expertise includes digital transformation leadership, ERP implementation, IT strategy development, cybersecurity enhancement, AI and RPA integration, M&A advisory, and cloud migration planning.

Question 5

How much experience does Richard have as a CIO and Transformation Director?

Accepted Answer

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.

Question 6

Why should you choose me as your interim CIO?

Accepted Answer

With over 34 years of experience, I bring a unique blend of commercial insight and technical expertise. I excel 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.

Question 7

Can I assist with ERP transformation and digital architecture?

Accepted Answer

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

Question 8

Am I available for fractional or advisory roles?

Accepted Answer

Yes, I am available for fractional CIO roles, board advisory positions, and strategic consultancy assignments. My recent engagements include private equity advisory, technology strategy formulation, and business transformation leadership.

Question 9

What is Richard's approach to IT strategy and transformation?

Accepted Answer

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.

Question 10

Does Richard work with startups or only large enterprises?

Accepted Answer

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.

Question 11

How can I contact Richard Keenlyside?

Accepted Answer

You can reach Richard via email at richard@rjk.info (mailto:richard@rjk.info)or through his website contact form.(https://rjk.info/contact)

Interim CIO & Transformation Director – Richard Keenlyside FAQ