Jack McCloskey

About Jack McCloskey

Enterprise Transformation Executive and Principal Consultant with 20+ years of experience leading complex modernization, delivery, and architecture initiatives across banking, federal, healthcare, telecom, and travel. I’ve helped organizations including Royal Caribbean, IRS, Bank of America, PNC, Lockheed Martin, Pegasystems, and Centene deliver measurable results through enterprise transformation, compliance-driven modernization, workflow automation, and large-scale systems integration.My background sits at the intersection of executive strategy, enterprise architecture, and business transformation. I’m strongest in regulated and high-stakes environments where stakeholder alignment, governance, delivery discipline, and operational impact matter most.Highlights include leading large-scale transformation programs, safeguarding 100M+ regulated records, supporting initiatives tied to $50M+ in portfolio value, and delivering more than $45M in verified savings through modernization and operational redesign.I’m best suited for Principal Consultant, Enterprise Transformation, Director/Senior Director, Practice Leadership, and executive delivery roles where organizations need a senior leader who can bridge business strategy, technology execution, and measurable outcomes.Core areas include enterprise transformation, digital modernization, financial services transformation, executive stakeholder engagement, regulatory and compliance-driven delivery, enterprise architecture, workflow automation, CRM/ERP modernization, and cross-functional leadership.

Experience

1. Enterprise Digital Transformation Lead

   Royal Caribbean Group

   Apr 2025 — Present · Miami, FL, US

   Leads four cross-functional teams (80+ staff) delivering enterprise-scale digital engagement initiatives that drive measurable improvements in delivery and performance. Designed and deployed enterprise JIRA dashboards now leveraged across the organization for sprint tracking, backlog management, and executive reporting. Enhanced visibility into velocity, capacity planning, and issue resolution, resulting in a 30% increase in delivery predictability. Supervised integration across ERP, CRM, and guest systems, aligning data workflows with enterprise objectives, while implementing governance and quality frameworks that improved sprint predictability and reduced resolution times. Partnered with business leaders and engineering teams to translate enterprise data needs into actionable, results-driven solutions.

Education

• Drexel University

  Master's of Science, Software Engineering

  2010 — 2012

• Penn State University

  Bachelor's of Science (B.S.), Information Sciences

  2004 — 2008

Skills

• Certified Senior System Architect
• Master Data Management
• Data Warehousing
• Hyperion Reports
• Subversion
• Java
• Web Services
• Dataflux
• Eclipse
• Sql
• Linux
• C#
• Xml Databases
• Oracle Reports
• Jira
• Web Development
• Sql Server Management Studio
• Oracle Pl/Sql Development
• Wsdl
• Data Mining
• Erp Oracle
• Git
• Css
• Sap
• Legacy System Conversion
• Visual Studio
• Maven
• Html5
• Xml
• Data Modeling
• Pasw
• Microsoft Sql Server
• Data Migration
• Oracle Sql
• Jquery
• Oltp
• Web Applications
• Data Analysis
• Agile Methodologies
• Oracle Olap