Transformation isn’t just about technology - it’s about people, vision, and the ability to turn ambition into measurable action. In this Q & A, Hamilton Jones, Head of Strategy (AI & Transformation) at Deepend, shares what really drives successful transformation. From overcoming human barriers to translating vision into practical roadmaps, Hamilton reveals why customer insight is the compass for lasting change, and how strategy can shape growth far beyond a single project.

1. When businesses seek transformation, what’s the most common barrier they face - and how do you help them overcome it?
The biggest barrier is human: fear, resistance, and misalignment across leadership. Technology is rarely the issue. I help overcome this by reframing transformation as continuous change, not a finite event. By focusing on clarity of vision, measurable outcomes, and empowering the “middle” of the organisation, we create alignment. My role is to bring external perspective and structured methods - customer insights, impact modelling, iterative design - that shift mindsets from “shiny new problems” to value-driven change. Transformation succeeds when people feel informed, empowered, and confident that what’s being built delivers tangible impact.

2. How do you turn a big-picture vision into a practical strategy that teams can act on?
I translate vision into action by creating a shared framework that links ambition to measurable outcomes. We start with clarity: what does success look like for leaders, customers, and staff? Then, we model the value and impact across horizons - quick wins, scalable practices, long-term transformation. Importantly, we codify this into iterative roadmaps, not fixed blueprints, so teams can adapt as conditions change. By designing strategy as a living, testable set of hypotheses, teams gain both direction and agency. It’s less about lofty slides, more about enabling every sprint, decision, and prototype to reinforce the larger ambition.

3. What role does customer insight play in shaping transformation strategies?
Customer insight is the compass for transformation. Without it, organisations risk building elegant solutions to the wrong problems. By integrating behavioural research, journey mapping, and real-time feedback loops, we ensure strategies respond to lived needs - not internal assumptions. At Deepend, we’ve seen that customer insight doesn’t just validate ideas; it prioritises where to invest, helps anticipate adoption barriers, and provides measurable signals of progress. Whether through AI-enabled analysis or traditional ethnography, insight connects the “why” of customer value with the “how” of organisational change, making transformation both relevant and sustainable.

4. Can you share a time where strategy directly influenced a client’s long-term success?
With Teachers Health, strategy reshaped their acquisition model. The market was highly competitive, and their digital experience lagged. We reframed the project around measurable acquisition uplift, grounding it in customer journeys rather than features. By retagging, improving UX flows, and aligning campaigns with digital tools, we cut drop-offs and nurtured member conversions. The result wasn’t just a better website; it was a sustainable acquisition engine aligned to customer needs. Strategy made the difference by connecting technology choices to growth outcomes, ensuring investments translated into long-term competitive parity and improved member experience.

5. What separates successful digital transformation from those that fail?
Successful transformations are anchored in three things: leadership alignment, customer-led design, and measurable impact. Failures usually stem from chasing technology for its own sake, underestimating human factors, or treating transformation as a one-off project. Winners embrace transformation as continuous change, measured through clear value and impact frameworks. They adapt iteratively, embedding small wins to build momentum. Critically, they ensure people - customers, staff, leadership - see and feel the benefits early. Transformation that sticks is less about the tech stack and more about aligning purpose, people, and progress into a coherent, continuously reinforced journey.