Head of IT Applications

Location: Milan, Italy – Hybrid working (2 days remote)
Compensation: €90,000 gross annual salary + 20% bonus
Contract: Executive-level position – CCNL Commercio

The Opportunity

We are supporting a growing, independent insurance group in the search for a Head of IT Applications, a key leadership role responsible for the evolution of the Group’s application landscape, technology investments and systems integration.

Operating in the insurance advisory and risk management sector, the Group is pursuing an ambitious growth strategy driven by acquisitions and continued investment in technology and innovation.

The successful candidate will combine strong technical expertise, in-depth knowledge of the insurance industry and proven leadership capabilities to shape the application roadmap, oversee strategic technology initiatives and ensure the effective integration of newly acquired businesses.

This is an opportunity to play a central role in the Group’s technology strategy, working closely with IT leadership and business stakeholders to drive scalability, operational efficiency and long-term technological development.

Key Responsibilities

1. Application Development & Architecture

• Define the strategic direction and technical roadmap for internally developed applications, ensuring alignment with business objectives.

• Provide architectural guidance and technical oversight to the internal development function, working through the relevant team lead.

• Establish development priorities and oversee delivery plans, software quality, security standards and project timelines.

• Promote best practices across the software development lifecycle, encouraging technical excellence, team autonomy and continuous improvement.

• Ensure consistency and scalability across the Group’s application architecture.

2. Data Migration & Business Integration

• Oversee data migration and application integration initiatives arising from acquisitions and business expansion.

• Validate integration strategies and migration plans, ensuring alignment with Group platforms and architectural standards.

• Monitor project risks, dependencies, timelines and delivery outcomes.

• Ensure data quality, business continuity and the effective transition from legacy systems to Group-wide platforms.

• Drive application consolidation and the decommissioning of redundant systems.

3. Third-Party Solutions & Vendor Management

• Lead the evaluation, selection and implementation of third-party application solutions.

• Assess technology options against business requirements, comparing external solutions with internal development alternatives.

• Evaluate integration requirements, security, scalability, total cost of ownership and expected business benefits.

• Manage key technology vendors, including commercial negotiations, contractual commitments and service performance.

• Oversee implementation programmes, stakeholder engagement, user adoption and the achievement of expected outcomes.

4. Strategy, Budget & Investment Management

• Develop and maintain the Group’s application roadmap, anticipating technology requirements arising from continued growth and acquisitions.

• Manage budgets, forecasts and technology investments across the areas of responsibility.

• Prioritise initiatives based on business value, financial impact, risk, dependencies and available resources.

• Monitor expenditure, identify variances and implement corrective measures where necessary.

• Provide clear recommendations to IT leadership and business stakeholders, outlining alternative solutions, costs, risks and strategic implications.

5. Leadership & Stakeholder Management

• Lead through the relevant team leads, setting direction and ensuring accountability for delivery and results.

• Build strong relationships with IT leadership, business stakeholders and external technology partners.

• Translate business needs into sustainable technology solutions, balancing strategic priorities with operational requirements.

• Develop team capabilities and foster a culture of ownership, collaboration and continuous improvement.

Candidate Profile

The ideal candidate will bring a combination of strategic vision, technical credibility and commercial awareness, with the ability to make informed technology decisions and drive their implementation in a growing, acquisition-driven environment.

Required experience and qualifications:

• At least 10 years of experience in IT application management, with direct responsibility for applications, teams, vendors and technology investments.

• Strong knowledge of the insurance industry, particularly insurance brokerage and/or MGA (Managing General Agent) environments, including relevant business processes and technology platforms.

• Solid understanding of application architecture, systems integration, data management and the software development lifecycle.

• Proven experience overseeing internal software development teams and making architectural and technical decisions.

• Demonstrated track record in data migration, application consolidation and post-acquisition business integration.

• Experience evaluating, selecting and implementing third-party software solutions.

• Strong vendor management, negotiation and commercial capabilities.

• Experience managing budgets, investment planning, financial forecasts and technology expenditure.

Key Competencies

• Strategic thinking: Ability to define a clear application roadmap aligned with business objectives and long-term growth.

• Technical leadership: Sufficient technical depth to challenge assumptions, evaluate alternatives and guide architectural decisions.

• Commercial acumen: Ability to assess business cases, optimise investments and negotiate effectively with technology partners.

• Execution and accountability: A pragmatic, results-oriented approach to managing priorities, risks and delivery.

• Stakeholder management: Strong communication and influencing skills, with the ability to engage effectively with both technical and non-technical stakeholders.

• People leadership: Ability to develop and empower teams, establish clear accountability and foster collaboration.

The Opportunity

The successful candidate will join a growing IT organisation and have a direct influence on the Group’s technology direction and investment priorities.

The role offers significant scope to shape the application landscape, support the integration of acquired businesses and drive the adoption of scalable technology solutions in a dynamic insurance environment.

This is an opportunity for an experienced IT leader to combine strategic responsibility with hands-on involvement in critical technology decisions, contributing directly to the Group’s continued growth and transformation.