CEO MONTHLY / OCTOBER 2025 13 Revolutionising Data Handling for Housing Providers Providing unrivalled insight into the ‘Big Six’ for social housing providers, TCW helps them interact with the data they need to assess risk more clearly. From fire and gas to electric and asbestos, the software platform it provides ensures compliance across the board. 90,000 documents are analysed by its system every week, with TCW then extracting the data and measuring it alongside the latest regulations, providing its clients with the facts and continuous monitoring to ensure compliance is achieved across their portfolios. Like most great business ideas, the seed for TCW was planted when Ryan Dempsey identified a need for something better, this during his time working as an assets and compliance head for the local authorities. Ryan managed thousands of assets across a diverse portfolio, and he sought out an improved way to help him understand the data in front of him and decide where to spend the investments. His vision of an evidence-based tool gave way to TCW, which would take unstructured data and turn it into detailed insights. “If something has stirred you so deeply that you feel compelled to build, hold on to that moment, it’s the spark that will keep you alive when things get tough, trust me.” As both the founder and CEO of the company, Ryan’s responsibility to TCW is multifaceted, but revolves primarily around protecting and advancing the ‘why’, the purpose that first led to the creation of the brand. Ryan explained: “That means more than just setting direction, it means rolling up my sleeves, diving into the complexities of compliance management, and showing through action that I can ‘walk the walk’.” Every CEO knows that real greatness occurs in those unseen hours, the late nights spent researching and building – not for recognition but to truly understand their craft and where they fit in. Ryan knows this more than most, as, at 43 years old, he has had a diverse career ranging from the police and the military through to undercover security. The insights these roles provided into the realities of risk, responsibility, and human consequence taught Ryan more than any book on leadership ever could. In this way, Ryan’s approach to leadership is truly exceptional, as he has not followed one school of thought or individual – he is simply himself. The culture created as a result of his team knowing that he is making decisions based on lived experience and with everyone’s best interest in mind is something special, and ensuring this environment is one where people can challenge freely and share ideas sees a team work together under common values. “I am very grateful for the people around me in TCW. You only have to spend five minutes in the company’s offices to be amped up and ready to go.” With TCW specialising in both compliance software and intelligent automation, it was only going to be a matter of time for the company had to look at integrating AI into its services, especially AI-enabled risk management. Ryan told us that his team have been researching AI for a few years now, being cautious in their approach but willing to embrace the technology out of recognition that it can add tangible value. This feeds into another cornerstone of Ryan’s leadership ethos: drive positive change with a ‘yes’. “Saying yes first creates opportunities that might otherwise never have presented themselves”, he explained. “Of course, it can sometimes take you in directions you hadn’t planned, but in my experience, those detours often open the most valuable doors.” Ryan shared: “Recently, I joined a peer group called the Duratus, which focuses on personal development. It has been an important influence, not because it tells you how to lead, but because it gives leaders and founders a safe space to share the challenges and uncertainties that are often hidden for most people in business. For me, this helps with the belief that leadership isn’t about having all the answers, it’s about being willing to listen, adapt, and grow, to make mistakes but to always fail forward.” The passion that runs deep within Ryan’s veins when he talks about TCW is in no way feigned, and one of the hardest things for this CEO to come to grips with is the fact that people think he is just there to sell them compliance software. Whilst profit and driving growth are obviously important to any business, TCW is about conviction and cementing itself as a partner to as many housing providers as possible, affording everyone in the realm of social housing a level of protection that not only minimises risk, but saves lives. Contact: Ryan Dempsey Company: TCW Web Address: https://tcwin.co.uk/ Aug25083 Ryan Dempesy, recognised in this feature as the Most Influential CEO 2025 – Social Housing Compliance (UK), is the brain behind TCW, a company specialising in turning information into insight for social housing providers. Having experienced first-hand the devastating outcomes of what happens when compliance is not achieved, Ryan founded TCW as a way of doing things better – benefiting clients through the provision of a platform that works without disrupting their workflows and within their current systems. We caught up with Ryan to find out more about his work.
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