Hiring an effective Director of Transformation
Bain Company Research found that whilst business transformations are not uncommon and up to one-third of companies are currently in some form of 'transformation' Only 12% meet the original ambition.
They go on to say that one of the strongest predictors of a transformation’s success is having the right people in the critical strategy roles, so look at your leadership and transformation and strategy leaders first.
The most common mistakes they cited were
- Not focusing on the critical roles
- Not looking beyond the star players
- Spending too little time thinking about the long-term vision for the future
Whilst a large number of companies now have Transformation Directors, or Head of Transformation roles, there is a growing support for the creation of the Chief Transformation Officer.
Hiring a Chief Transformation Officer
The role of the Chief Transformation Officer is now one of the most critical appointments a leadership team can make. In an era of rapid digital disruption, shifting customer expectations, regulatory change, and economic uncertainty, a CTO is often tasked with delivering the initiatives that determine whether an organisation thrives, stagnates, or loses market position. Hiring the wrong person can cost millions, derail strategic plans, and damage stakeholder confidence.
At Douglas Jackson, we specialise in executive search for Chief Transformation Officers and transformation leadership teams across regulated and customer-led markets, including Utilities, Housing, Insurance, Financial Services, and Technology. We know that large-scale transformation is as much about cultural alignment and political navigation as it is about programme delivery. The most successful Chief Transformation Officers are visionaries who can also execute, building trust across the boardroom, the frontline, and key stakeholder groups.
The challenges of hiring a Chief Transformation Officer
Many transformations fail not because of poor strategy, but because the leader driving it lacked the influence, resilience, or alignment with the organisation’s culture to see it through. Typical challenges include:
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Ambiguity at the top – unclear priorities or shifting objectives from leadership.
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Cultural resistance – entrenched ways of working and siloed thinking.
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Transformation fatigue – stakeholders tired of change initiatives that overpromise and underdeliver.
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Retention risk – talented leaders leaving before transformation benefits are realised.
Our proven approach to recruiting transformation leaders
We go beyond CVs and role profiles to uncover the qualities that matter most: the ability to align transformation goals with business strategy, navigate complex stakeholder environments, and deliver measurable outcomes. Our rigorous search process, market intelligence, and deep network ensure we present a shortlist of leaders who will perform and stay the course.
Two essential tips for hiring a successful CTO:
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Define success early and make it measurable. Set clear, agreed outcomes for the first 6, 12, and 24 months so your transformation leader is aligned from day one.
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Hire for influence, not just technical capability. The ability to inspire, persuade, and overcome resistance is the deciding factor in whether transformation becomes reality.
With over two decades’ experience in executive search for senior transformation roles, Douglas Jackson is the go-to search partner for organisations that want to hire diverse, high-impact leaders who stay longer, perform better, and create lasting value. Whether you’re leading a digital transformation, operational restructuring, cultural change, or customer experience evolution, we can help you identify, attract, and secure the transformation leader your business needs to succeed. When transformation is customer-led, a Chief Customer Officer can be key.
Not yet sure whether you need a Chief Transformation Officer, or a change of COO? Discover how to recruit a Chief Operating Officer who can optimise operations.
Planning and Insight
Customer and Operations
Transformation and Change
