Head of Transformation Delivery - Cayman Islands

Overview of role

We are seeking an exceptional Director of Transformation to lead and shape the strategic direction of our global Transformation Delivery function. This is a high-profile leadership opportunity for an experienced transformation professional with a proven track record of delivering complex enterprise-wide programmes, driving operational excellence, and building high-performing global teams.

Reporting directly to the Chief Transformation Officer, the Director of Transformation will oversee the firm’s transformation roadmap and portfolio of strategic programmes and projects across multiple jurisdictions. The successful candidate will play a pivotal role in enabling organisational change, embedding delivery excellence, and ensuring transformation initiatives achieve measurable business value. This role carries significant responsibility for portfolio governance, strategic planning, financial management, stakeholder engagement, and resource leadership, while ensuring transparency and alignment throughout the full transformation delivery lifecycle. The Director of Transformation will act as a trusted advisor to senior leadership, partnering closely with C-suite executives, operational leaders, and business stakeholders to shape and execute initiatives that support the organisation’s long-term strategic 

Duties, Responsibilities & Person Specification

Director of Transformation  

Transformation 

Salary Range US$180,000–US$250,000

• Set and drive the strategic direction for the Transformation Delivery function, leading execution of the firm’s global transformation roadmap
• Oversee a portfolio of transformation programmes and projects, ensuring delivery against timelines, budgets, quality standards and strategic objectives
• Translate business strategy into actionable delivery plans with clear outcomes, benefits and measurable ROI
• Establish and continuously enhance portfolio, programme and project governance frameworks across the organisation
• Lead end-to-end transformation delivery, including planning, resource allocation and value realisation tracking
• Own and manage the Transformation Delivery budget, including forecasting and performance against investment objectives
• Build, lead and develop a high-performing global team, providing coaching, mentoring and clear leadership structure
• Foster a culture of accountability, collaboration, innovation and continuous improvement
• Act as a trusted advisor to senior leadership and C-suite stakeholders on transformation strategy, delivery and governance
• Build strong relationships across functions and jurisdictions, ensuring alignment and effective stakeholder engagement
• Drive adoption of best practice delivery methodologies, including Agile, Lean and PRINCE2
• Promote continuous improvement, innovation and the use of tools and technologies to enhance delivery effectiveness

Education, Skills & Experience

• Bachelor’s or Master’s degree in a relevant discipline (e.g. Business, IT, Finance, Management) or equivalent experience
• Professional certifications (e.g. PRINCE2, Agile) highly desirable
• Minimum 10 years’ experience leading large-scale transformation programmes or enterprise change initiatives,
• At least 5 years in a senior leadership role with responsibility for strategy, budgets, operations and team leadership
• Proven experience managing complex, global transformation portfolios and multi-jurisdictional teams
• Background in professional services, consulting, financial services or legal environments preferred
• Strong strategic mindset with the ability to translate business priorities into effective delivery
• Demonstrated experience engaging and influencing executive-level stakeholders and managing high-profile relationships
• Expertise in programme and project delivery methodologies (Agile, Lean, PRINCE2 or equivalent).
• Deep understanding of business transformation, operational change, and emerging technologies.
• Strong commercial and financial acumen, including budget ownership, forecasting and ROI management
• Exceptional leadership and people management skills, with the ability to motivate and develop high-performing teams
• Excellent communication, presentation and stakeholder engagement skills including executive-level presentation capabilities.
• Strong analytical, planning and problem-solving capabilities, with a focus on outcomes and value delivery
• Adaptable and solutions-oriented approach, with a commitment to continuous improvement and innovation
• Collaborative and able to build relationships across functions, cultures, and geographies.
• Strong commitment to continuous improvement, innovation, and delivery excellence

Walkers offers a dynamic working environment with opportunities for career progression and an excellent remuneration package, including a discretionary performance-based bonus, pension and fully covered health insurance for employees and 5 weeks' vacation. Remuneration will commensurate with qualifications and experience.

We invite applications from suitably qualified Caymanians or residents with Employment Rights. Please note that Walkers will not accept any applications received from agencies at this time.

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