Jonathan Díaz

Enterprise Digital Transformation & AI Initiatives

• Led strategic planning and cross-departmental coordination for implementing Microsoft 365 Copilot at the Puerto Rico Department of Education (PRDE), benefiting over 200,000 users. Improved administrative and academic workflows through generative AI adoption, significantly enhancing productivity, digital maturity, and data-driven decision-making across the organization.

Government Modernization & Infrastructure Projects

• Managed the deployment of one of Puerto Rico's largest Voice-over-IP (VoIP) projects for PRDE, installing over 8,000 Cisco phones in 900 schools and facilities. Restored communication capabilities after Hurricane María and upgraded the Call Center for HR and Special Education services.
• Developed the first and most comprehensive School Facility Management Solution for PRDE, offering real-time insights into the needs of over 850 schools and unifying requests from school directors, regional offices, OMEP, and AEP into a single operational platform.

Process Optimization & Operational Efficiency

• Supported the Technology Office of the Corporación del Fondo del Seguro del Estado (CFSE) in establishing its Project Management Office (PMO), structuring 20–30 initiatives, and centralizing them into a unified project platform within 2–4 weeks. Introduced governance, standardized milestones, and enhanced cross-department visibility, resulting in improved operational consistency and strategic alignment.
• Led transformation initiatives for CFSE’s Insurance and Collections Departments using the SIFRE platform, automating payroll reporting and collection notifications, and cutting employer billing cycles from months to seconds.

Digital Platforms, Citizen Services & Public Engagement

• Led the implementation of the Integrated Service Management Monitor and Supplier Portal for PRDE, PRASA, and the Municipality of San Juan, digitizing and standardizing the processing of over 10,000 monthly invoices. Achieved approximately $60M in savings through anomaly detection, leak identification, and consumption optimization.
• Led digital modernization for the Lotería Tradicional de Puerto Rico (LTPR), including upgrades to its core operations, public website, and mobile app (over 100,000 downloads). Reduced manual workload by 80% and improved citizen engagement through better digital service channels.
• Led the implementation and ongoing support of the Sistema Integrado de Lotería Electrónica (SILE) for the Lotería Electrónica de Puerto Rico (LEPR), automating and centralizing the merchant licensing process. Modernized operational modules and enhanced internal controls through comprehensive digitization.

Enterprise Content Management (ECM) & Banking Data Operations

• Led the development and implementation of the Enterprise Content Management (ECM), Printing, and Mailing Outsourcing Business Line for Banco Santander and Island Finance, generating $12M in revenue over 12 years. Oversaw large-scale operational services, ensuring reliability, compliance, and continuous client renewal.
• Managed operational processing for more than 2,000,000 monthly bank documents, including forms, letters, statements, images, and over 20,000 reports. Directed project and operational planning across the entire Business Line (BL), ensuring accuracy, timeliness, and regulatory adherence.
• Oversaw more than 40TB of live-replicated banking data, managing high-availability environments across parallel facilities. Ensured uninterrupted operations, robust disaster recovery capabilities, and data integrity throughout all regulated processes.
• Delivered projects on time and within budget for 12 consecutive years, with consistently high-quality deliverables, documentation, and stakeholder alignment—resulting in annual service renewals from major financial institutions.

Large-Scale Banking Systems Modernization & Regulatory Platform Support

• Led the development and implementation of multiple ECM-driven modernization projects for retail and commercial banking systems, operating within a strict regulatory environment receiving over 5,000,000 monthly internal and external user hits. Enhanced stability, data flows, and digital customer experience.
• Designed and deployed Data Validation processes supporting multiple banking products, enabling error detection, prevention, and resolution for systems handling financial data of more than 300,000 customers. Reduced operational risk through enhanced data integrity and validation logic.

Data Migration, Segregation & Portfolio Transition Projects

• Managed the migration and extraction of 5.8 million JetBlue credit card statements from the OnDemand system as part of the portfolio transition from Banco Santander to Banco Popular (2013–2020). Ensured data accuracy, compliance, and timely delivery throughout the migration window.
• Led the Content Management Data Segregation and Migration initiative for FirstBank-owned entities, supporting the Banco Santander acquisition. Executed a multi-stage migration of 60TB of historical data over a 6- to 9-month period, maintaining strict continuity, compliance, and data governance at enterprise scale.

Content Management Operations & Enterprise Systems Engineering

• Led day-to-day operations, design, development, testing, installation, and maintenance of the OnDemand (CMOD) application and its underlying technical infrastructure, supporting enterprise-level content management for high-volume financial institutions. Provided IT consulting specializing in the implementation and administration of high-technology solutions and enterprise platforms.
• Served as the technical lead for all CMOD upgrades, enhancements, and migration strategies, ensuring high availability and adherence to established business and technology service levels. Oversaw planning and execution of improvements that increased system performance, stability, and scalability.
• Provided technical leadership, staff oversight, and development guidelines for both internal teams and external vendors, ensuring consistent delivery of support and development services. Enabled seamless integrations across internal systems, third-party partners, and multi-platform environments related to Content Management.
• Collaborated closely with the DB2 Database Administration team to maintain a stable, secure, and optimized database infrastructure supporting the CMOD ecosystem. Ensured performance alignment with high-volume operational demands and regulatory requirements.
• Ensured full compliance with internal Audit, Risk, and Information Security standards, maintaining secure processing of sensitive financial data and supporting audit-ready environments across all CMOD components.
• Served as the primary Systems Engineer for Disaster Recovery (DR) planning and execution, validating the recoverability of the OnDemand environment through DR exercises and ensuring alignment with business continuity objectives and recovery time requirements.

IT Specialist & Senior IT Specialist – Early Career Roles

• Provided end-user support, systems administration, and day-to-day operational maintenance across government agencies, financial institutions, and telecommunications environments.
• Delivered help desk services supporting 500+ users across 25+ applications and platforms, managing 5–15 calls per hour based on operational demand.
• Configured hardware, software, and networked workstations for 200+ employees, ensuring reliable system performance and user readiness.
• Oversaw installation, upgrades, and maintenance of applications and network components as part of organization-wide IT modernization efforts.
• Explained technical concepts in clear, accessible terms to non-technical stakeholders, improving user adoption, understanding, and support efficiency.