Director of Transformation - Cayman Islands

Director of Transformation - Cayman Islands
We are a leading international law firm for global corporations, financial institutions, capital market participants and investment fund managers. With a global presence spanning the Americas, Europe, the Middle East and Asia, we advise on the laws of Bermuda, the British Virgin Islands, the Cayman Islands, Guernsey, Ireland and Jersey.

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 strategy.

Duties, Responsibilities & Person Specification
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.

Walkers global is an equal opportunity employer. Equality and diversity are key to our global identity and an integral part of our goal to continue being an employer of choice. We are committed to a work environment that supports all individuals irrespective of gender, ethnicity, nationality, race, religion, marital status, age, disability, pregnancy, sexual orientation, gender identity or any other applicable legally protected characteristics. We make every effort to ensure that employment opportunities are open and accessible to all purely on the basis of personal ability.

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