We have a fantastic opportunity for an experienced IT professional to join our IT team at Mediolanum as Head of Technology Delivery.
The Head of Technology Delivery is accountable for the end-to-end execution of the technology delivery portfolio, ensuring that strategy is translated into predictable, transparent, and value-driven outcomes. This role operates as the de facto deputy to the Chief Information Officer (CIO) from day one, providing strategic and operational leadership across delivery, governance, and capability management. The role is pivotal in strengthening delivery discipline, increasing transparency, and ensuring the organisation retains ownership of its technology strategy, knowledge, and decision making capability.
This is an outstanding opportunity to become part of a dynamic, expanding team that leverages innovative technology to drive business transformation and innovation. Successful performance over the initial 18-month period, measured against clearly defined objectives and outcomes, may also position the individual as a strong candidate for consideration for the title of Deputy Chief Information Officer.
Principal Duties of the position, including but not limited to:
* Own and lead the end-to-end technology delivery function, ensuring consistent, high quality execution across all initiatives and programmes.
* Translate IT and organisational strategy into actionable delivery plans with clear milestones, dependencies, and value metrics.
* Drive delivery predictability while enabling appropriate agility to respond to changing business priorities.
* Drive the delivery of complex, cross functional technology programmes (date, applications and infrastructure), acting as executive sponsor where required, and ensuring scope, resourcing, risk management, and schedule discipline are in place.
* Lead delivery using modern methods (Agile, DevOps), establish meaningful metrics, and run regular retrospectives to continually improve throughput, quality, and cycle time.
* Act as trusted deputy to the CIO, supporting decision making, prioritisation, and executive engagement and represent the CIO when required at senior leadership forums, ensuring continuity of leadership and direction.
* Support the CIO in protecting and strengthen internal ownership of Technology and digital strategy, Architecture and solution integrity and Institutional knowledge and critical competencies.
* Contribute actively to strategic planning, investment discussions, and long term technology roadmaps.
* Mature delivery and governance processes across demand intake, prioritisation, execution, and benefits realisation.
* Ensure full transparency of the delivery journey, providing clear, regular insight into status, risks, dependencies, and outcomes.
* Establish disciplined reporting that enables effective oversight by the CIO, Executive Committee, and Board.
* Embed robust project and portfolio governance (status reviews, RAIDD management, stakeholder communications) and align with security and regulatory frameworks (e.g., ISO/IEC 27001, DORA, GDPR) in partnership with risk and compliance functions.
* Lead capacity, resource, and demand planning, ensuring alignment between strategic priorities, delivery commitments, and available capabilities.
* Enable informed trade offs through data driven insight into workload, constraints, and future demand.
* Balance near term delivery needs with longer term sustainability and capability development.
* Review and enhance the balanced sourcing model, ensuring appropriate use of external consultants while avoiding over reliance or loss of control.
* Ensure external partners are used to accelerate delivery and build capability, not to replace core accountability.
* Act as an "intelligent client" with strong vendor management and commercial acuity; challenge suppliers, assure quality, and ensure outcomes remain aligned to organisational priorities.
* Maintain strong internal capability to assure delivery quality and make informed decisions across the portfolio.
* Enforce current practices of knowledge transfer, documentation, and capability uplift as standard practice across all engagements.
* Support the ongoing data governance program (data quality, metadata management, master data management) so delivery outcomes are supported by trustworthy data.
* Serve as a trusted advisor to senior business leaders, translating business deliverables into technology initiatives and coordinating prioritisation to maintain alignment with strategic goals and promote strong partnerships between IT and business functions; leading cross disciplinary squads spanning engineering, data, security, risk, and operations to land enterprise wide change.
* Act as a change leader who guides users and stakeholders through technology driven organisational change with clear communications and adoption plans.
* Support and enhance the execution of the enterprise data strategy to improve analytics and reporting.
* Champion trusted analytics, BI, and AI—ensuring governance, model risk, and ethical use are embedded—so product teams and business functions can make data driven decisions at pace.
* Encourage pragmatic innovation and establish a culture of experimentation with guardrails; measure impact and scale what works.
* Lead and mentor the Technology Delivery team and technical experts across the department; clarify roles, accountability, and career paths.
* Build a high performance, inclusive culture focused on collaboration, learning, and professional growth.
Skills and Competencies:
* Broad knowledge across enterprise IT (data platforms, cloud, applications) and software delivery lifecycle.
* Familiarity with modern data architectures (e.g., lakehouse, pipelines), analytics/BI platforms, and secure engineering practices.
* Strong understanding of relevant regulations/standards (e.g., ISO/IEC 27001, DORA, GDPR) and the ability to translate requirements into actionable compliance within delivery.
* Exceptional communication and stakeholder management; credible at C suite/Board level.
* Strong vendor management and negotiation skills.
* Strategic thinker with a pragmatic, hands on approach to achieving outcomes.
Qualifications and Experience:
* Bachelor's or Master's degree in Computer Science, Information Systems, or related field; an MBA or relevant postgraduate qualification is a plus.
* Extensive experience (15+ years) in IT leadership roles covering strategic planning, governance, and programme delivery in complex, regulated environments.
* Proven track record delivering large scale transformation and managing multi disciplinary teams.
* Domain experience in asset management; knowledge of custody and fund accounting is advantageous.