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Open nowFirst seen 5 days ago

Director of Digital Transformation — Insurance & Investments

thehivecareers.co2,951 open roles

Where
George Town, Cayman Islands, Remote
Work mode
Remote
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Your applicationOpen nowDirector of Digital Transformation — Insurance & Investmentsthehivecareers.co · George Town, Cayman Islands, Remote

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The clock on this job

Early applications get read.

12.3% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.3%7 days
  4. 19.3%14 days
  5. 35.6%30 days
  6. 58.1%60 days
This job: first seen 5 days ago

The posting

Job Summary

The Director of Digital Transformation leads enterprise-wide digital transformation initiatives, using technology, data, automation, and redesigned business processes to improve operational efficiency, customer experience, scalability, and business performance.

Within Insurance & Investments, the role focuses on transforming insurance, investment, finance, customer, and corporate processes through digital platforms, automation, analytics, AI, cloud, and integrated enterprise systems.

Key Responsibilities

Develop and execute the organization's digital transformation strategy and roadmap.

Identify opportunities to digitize, automate, and redesign business processes.

Lead enterprise-wide digital transformation programs and portfolios.

Partner with business, IT, investment, insurance, finance, risk, and operations leaders.

Drive modernization of legacy systems, platforms, and technology architecture.

Lead digital customer experience initiatives across web, mobile, portals, and self-service channels.

Implement workflow automation, RPA, AI, machine learning, and intelligent process solutions.

Oversee digital transformation of insurance processes including underwriting, policy administration, claims, and customer servicing.

Support digitalization of investment and asset-management processes, portfolio reporting, research, and client servicing.

Drive data, analytics, BI, and AI-enabled decision-making.

Lead cloud adoption, APIs, systems integration, and platform modernization.

Establish transformation governance, KPIs, benefits tracking, and program reporting.

Manage transformation budgets, vendors, consultants, and strategic technology partners.

Identify and manage transformation risks, dependencies, and change impacts.

Lead organizational change management, stakeholder engagement, and digital adoption.

Ensure transformation initiatives comply with cybersecurity, privacy, regulatory, and risk requirements.

Build a culture of continuous improvement, innovation, and digital adoption.

Present transformation progress, investment requirements, benefits, and risks to executive leadership.

Ideal Candidate Profile

10–15+ years of experience in digital transformation, technology, consulting, business transformation, or financial-services technology.

5+ years in Director of Digital Transformation, Digital Transformation Lead, Head of Digital Transformation, Chief Digital Officer, Technology Director, or equivalent roles.

Experience in insurance, investment management, asset management, banking, wealth management, or financial services strongly preferred.

Strong experience in:

Digital transformation strategy

Business process transformation

Digital operating models

Technology modernization

Automation / RPA

AI & analytics

Cloud transformation

Data transformation

Customer experience / digital channels

Change management

Program & portfolio management

Systems integration

Experience leading complex, multi-functional transformation programs.

Strong business partnering and executive stakeholder-management skills.

Experience managing budgets, vendors, consultants, and transformation teams.

Bachelor's degree in Technology, Computer Science, Business, Engineering, Finance, or related discipline; MBA or relevant transformation/digital certifications advantageous.

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