At 5411 Hub, we are currently looking for a Chief Technology Officer (CTO) to join an insurance company based in Costa Rica, in a strategic leadership role focused on driving the organization’s technology vision and supporting its digital transformation journey.

📍 Location: San José, Costa Rica
💼 Work Modality: Hybrid
🕘 Schedule: Full Time
🌎 English: Desirable

About the role

We are seeking a senior technology leader with a strong strategic mindset and proven experience leading technology teams and digital transformation initiatives within complex organizations. This role will play a key part in defining the company’s technology strategy, ensuring scalability, efficiency, and modernization across platforms, systems, and business processes.

The CTO will be responsible for leading the technology function, driving innovation, and working closely with executive leadership to align technology capabilities with business objectives.

Key responsibilities

• Define and lead the company’s technology strategy in alignment with business goals.
• Lead technology, infrastructure, systems, and/or development teams, fostering a culture of innovation and continuous improvement.
• Oversee the evolution and modernization of platforms, applications, and overall technology architecture.
• Ensure operational continuity, system availability, security, and scalability across the organization.
• Identify opportunities for automation, optimization, and digital transformation.
• Partner closely with business leaders to understand priorities and translate them into effective technology solutions.
• Manage technology vendors, strategic partners, and key implementation projects.
• Establish governance, security, architecture, and technology best practices.
• Monitor KPIs related to performance, quality, efficiency, and technology operations.

Requirements

• Strong experience in senior technology leadership roles such as CTO, Head of Technology, IT Director, or similar.
• Proven track record leading technology teams and digital transformation projects.
• Experience defining technology strategy, architecture, infrastructure, systems, and platform modernization.
• Ability to connect technology decisions with broader business objectives and long-term organizational goals.
• Experience in regulated industries, ideally insurance, financial services, or similarly complex environments.
• Strong leadership, autonomy, stakeholder management, and strategic decision-making capabilities.
• Based in Costa Rica or available to work in a hybrid model in the capital city.

Nice to have

• Previous experience in insurance companies or strong understanding of the insurance business.
• Background in digital transformation, legacy system modernization, or implementation of new enterprise platforms.
• Knowledge of information security, IT governance, and business continuity practices.
• Ability to work with senior stakeholders and lead organizational change initiatives.

If you are interested in learning more about this opportunity, we’d love to hear from you.

Skills: CTO, Technology Strategy, Digital Transformation, IT Leadership, Infrastructure, Cybersecurity, Systems Modernization, Stakeholder Management, Innovation