Head of Digital — Insurance & Investments at TheHiveCareers · Cayman…

Job Summary

The Head of Digital is responsible for developing and executing the organization's digital strategy, leading digital products and channels, and driving technology-enabled improvements in customer experience, business growth, and operational efficiency.

In Insurance & Investments, the role focuses on digitizing the customer and investor lifecycle—from onboarding and KYC through policy servicing, claims, payments, investment transactions, portfolio monitoring, and customer self-service. The Head of Digital bridges business strategy, digital products, technology, data, customer experience, and innovation.

Key Responsibilities

Digital Strategy & Transformation

Develop and execute the enterprise digital strategy and roadmap.

Align digital initiatives with corporate, insurance, investment, and commercial objectives.

Identify opportunities to digitize manual and legacy processes.

Lead digital transformation programs across business functions.

Establish digital operating models, governance, standards, and KPIs.

Evaluate emerging technologies including AI, automation, cloud, APIs, and fintech/insurtech solutions.

Digital Products & Platforms

Own the strategy and lifecycle of digital products and customer-facing platforms.

Lead digital portals, mobile applications, websites, and self-service channels.

Drive digital onboarding, account opening, policy servicing, claims, payments, and customer communications.

Partner with Technology/Engineering on APIs, integrations, cloud platforms, and application modernization.

Ensure digital platforms are scalable, secure, reliable, and user-friendly.

Customer & Investor Experience

Lead digital customer experience (CX) and journey transformation.

Map and optimize customer and investor journeys.

Improve digital adoption, conversion, engagement, and retention.

Use customer data and analytics to personalize digital experiences.

Establish omnichannel experiences across web, mobile, branch, agent, broker, and contact-center channels.

Insurance Digitalization

Digitize policy acquisition and servicing.

Develop digital quotation and application journeys.

Support digital underwriting and risk assessment.

Enable online claims submission and claims tracking.

Develop agent/broker portals and digital distribution channels.

Improve digital payments, billing, renewals, and customer self-service.

Partner with InsurTech providers and digital distribution platforms.

Investments & Wealth Management

Lead digital investor onboarding and KYC journeys.

Develop investor and wealth-management portals.

Enable digital account opening and investment transactions.

Support digital portfolio dashboards and performance reporting.

Improve online investor communications and self-service.

Integrate investment, portfolio, custody, CRM, and market-data platforms.

Data, Analytics & AI

Partner with Data & Analytics leadership to use customer and operational data.

Apply AI, machine learning, automation, and predictive analytics to digital journeys.

Use analytics to improve conversion, customer engagement, product performance, and retention.

Establish digital performance dashboards and data-driven decision-making.

Digital Product Delivery

Introduce Agile, Scrum, product management, and user-centered design practices.

Establish product roadmaps, priorities, business cases, and delivery metrics.

Lead UX/UI and design teams or strategic partners.

Coordinate cross-functional product squads involving business, technology, data, risk, and operations.

Ensure continuous product improvement based on customer feedback and analytics.

Governance, Risk & Security

Ensure digital platforms comply with financial-services regulations.

Work closely with CISO, Risk, Compliance, Legal, and IT teams.

Address cybersecurity, privacy, identity, access, and third-party risks.

Ensure digital products comply with data protection and regulatory requirements.

Maintain appropriate controls around digital transactions and customer information.

Leadership & Commercial Management

Lead digital/product/UX teams and transformation programs.

Manage digital budgets, vendors, consultants, and technology partners.

Establish partnerships with fintech, insurtech, investment technology, and SaaS providers.

Track ROI, adoption, revenue contribution, cost savings, and business outcomes.

Report digital strategy, performance, risks, and investment requirements to executive leadership.

Insurance & Investments Digital Priorities

Area Digital Focus

Insurance Sales Digital quotation, applications, e-signature, online purchasing

Policy Servicing Customer portals, mobile servicing, renewals, payments

Claims Digital FNOL, claims tracking, document upload, automated workflows

Distribution Agent/broker portals, digital sales, embedded insurance

Customer Experience Omnichannel, personalization, self-service

Investments Digital onboarding, KYC, account opening, transactions

Wealth Management Investor portals, portfolio dashboards, digital advice

Analytics Customer behavior, conversion, retention, product analytics

Automation RPA, AI, workflow automation, straight-through processing

Technology Cloud, APIs, microservices, mobile/web platforms

Security Identity, authentication, privacy, cybersecurity

Innovation Fintech, InsurTech, AI, emerging digital technologies

Ideal Candidate Profile

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

5+ years in senior digital leadership.

Proven experience developing and executing enterprise digital strategies.

Strong background in digital products, platforms, customer experience, and digital channels.

Experience leading large-scale digital transformation initiatives.

Strong knowledge of:

Digital Product Management

Customer Experience / CX

UX/UI

Mobile & Web Platforms

Digital Onboarding

APIs & Integrations

Cloud Technology

Agile/Scrum

Data & Analytics

AI & Automation

CRM

Digital Payments

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

Strong commercial understanding of customer acquisition, conversion, retention, and digital revenue.

Experience managing technology vendors and strategic digital partners.

Bachelor's degree in Technology, Computer Science, Engineering, Business, Digital Transformation, or related discipline; MBA/master's preferred.