David Winter is Head of Data at Direct Line, where he leads the organisation’s data strategy with a focus on delivering tangible business value and enabling better decision-making across the enterprise.
David has worked extensively with data, spanning analysis, modelling, and solution design. While his career path has been varied, a consistent theme has been maximising the return on technology investment by ensuring data is applied to solve real business problems. As data has become an increasingly critical organisational asset, this value-led approach has underpinned his work, linking insight directly to operational efficiency, strategic growth and improved outcomes.
David holds a clear belief that technology should act as an enabler rather than a barrier. He focuses on empowering teams closest to customers and core processes with the insight and tools they need to act confidently. This principle shapes his approach at Direct Line, where the data strategy prioritises accessible, democratised data capabilities alongside strong governance and reliability.
A key element of his leadership is building data confidence across the organisation. David has championed learning and development frameworks and platforms designed to raise data literacy across all roles, recognising that sustainable impact depends as much on people and capability as it does on platforms and architecture.
As a data and AI leader, which traits and skills do you think matter most, and which of those have been most influential for you in your current position?
“The ability to speak the language of the business; it’s not about technical mastery, but the ability to tell a compelling story about data’s impact on growth, risk, and innovation.
“From a value perspective, insights from data should be framed in terms of business outcomes, not algorithms or models.
“Data storytelling is one of the most important skills any data professional should develop and harness regardless of their role or position in the organisation. The ability to apply context to data and turn it into insight and information that can drive efficiency, innovation, and competitive advantage.
“Securing ExCo approval and funding for the data strategy at Direct Line was only possible through explaining to a largely non-technical ExCo board. In real-terms, how investment in data technologies would reduce risk and lead to a direct improvement to the bottom-lines of their business areas.”
Reflecting on your career, what is one non-traditional piece of advice (outside of technical skills) you would give to an aspiring data or AI leader aiming for the C-suite?
“Build relationships before you need them. Ensure peers across the organisation, including those in functions not immediately seen as critical to the success of a data strategy, are aligned with your vision and understand the ‘so what’ behind your objectives and what it means to them.
“At some point, you will need their support, and having informed, engaged allies when it matters can make all the difference.”