Head of Digital Transformation — Insurance & Investments

Job Summary

The Head of Digital Transformation leads the organization's enterprise-wide digital transformation agenda, connecting business strategy with technology, data, automation, and process redesign.

In an Insurance & Investments environment, the role focuses on modernizing insurance and investment operations, improving customer and employee experiences, automating processes, modernizing legacy systems, and using data, AI, cloud, and digital platforms to improve business performance.

Key Responsibilities

Develop and execute the enterprise digital transformation strategy and roadmap.

Lead a portfolio of strategic digital transformation programs across the organization.

Identify opportunities for process digitization, automation, simplification, and optimization.

Partner with Insurance, Investments, Finance, Risk, Compliance, Operations, HR, and IT leadership.

Lead modernization of legacy applications, platforms, workflows, and operating processes.

Drive digital customer journeys across web, mobile, portals, and self-service platforms.

Lead automation initiatives using RPA, AI, machine learning, workflow automation, and intelligent technologies.

Transform insurance processes such as underwriting, policy administration, claims, distribution, and customer servicing.

Support digital transformation across investment/asset management, portfolio management, reporting, research, and client servicing.

Drive data transformation, analytics, business intelligence, and AI-enabled decision-making.

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

Establish transformation governance, KPIs, milestones, benefits realization, and executive reporting.

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

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

Identify transformation risks, dependencies, resource requirements, and implementation challenges.

Ensure digital initiatives align with cybersecurity, privacy, regulatory, risk, and governance requirements.

Promote innovation and a culture of continuous improvement.

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

Ideal Candidate Profile

12–18+ years of experience across digital transformation, technology, business transformation, consulting, or financial-services technology.

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

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

Strong experience in:Digital transformation strategyBusiness/process transformationTechnology modernizationDigital operating modelsAutomation / RPAAI & machine learningData & analyticsCloud transformationDigital customer experienceChange managementProgram/portfolio managementSystems integration

Demonstrated success leading complex, enterprise-wide transformation programs.

Strong executive stakeholder and business-partnering capabilities.

Experience managing significant budgets, vendors, consultants, and multidisciplinary teams.

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