Jack McCloskey - Enterprise Transformation Executive

Jack McCloskey

Enterprise Transformation Executive | Digital Strategy & Delivery Leader

20 years leading digital modernization, Agile delivery, and data strategy for Royal Caribbean, IRS, Centene, Lockheed Martin, and Pegasystems.

$50M+ Portfolio
$45M+ Verified Savings
500+ Team Members Led
Aventura, FL

Executive Summary

Enterprise Transformation Executive with 20 years of experience leading digital modernization, Agile delivery, and data strategy for Royal Caribbean, IRS, Centene, Lockheed Martin, and Pegasystems.

Recognized for driving $50M+ in portfolio value and $45M+ in verified cost savings via automation, compliance modernization, and ERP/CRM integrations. Led global teams of 500+, built governance securing 100M+ federal records, and unified strategy & execution for measurable CX and operational gains.

A proven leader who inspires transformation through clarity, accountability, and results.

Core Leadership Competencies

Strategy & Vision

  • Enterprise Portfolio Management
  • KPI / OKR Frameworks
  • Transformation Roadmaps

Digital Transformation

  • ERP / CRM Modernization
  • Data Integration & Analytics
  • Enterprise Automation

Leadership & Culture

  • Executive Stakeholder Alignment
  • Agile at Scale
  • Global Team Leadership

Governance & Delivery

  • Risk & Compliance
  • HIPAA / SOC2 / GDPR
  • Process Reengineering

Education & Certifications

馃帗 Education

M.S., Software Engineering
Drexel University

B.S., Information Sciences & Technology
Penn State University

馃弳 Certifications

Six Sigma Yellow Belt 路 PSM 路 Pega CSSA 路 CPBA 路 CPM 路 CDA

Connect

Consulting Services

Jack offers tailored enterprise transformation consulting, including:

  • Digital strategy & roadmap development
  • ERP/CRM modernization & integration
  • Agile delivery at scale
  • Data analytics & automation
  • Compliance modernization (HIPAA, SOC2, GDPR)
  • Change management & executive alignment
  • Operational excellence & cost optimization

Industries served: Travel, Healthcare, Federal, Technology, and Fortune 500 clients.

See Platform Features or Documentation for more on our approach.

Current Focus

Leading digital engagement transformation at Royal Caribbean; available for select advisory engagements.

Frequently Asked Questions

What is Jack's consulting approach?

Jack combines executive vision with hands-on delivery, focusing on measurable outcomes, stakeholder alignment, and sustainable transformation. Each engagement is tailored to client needs, leveraging proven frameworks and industry best practices.

Which industries does Jack serve?

Jack has led transformation initiatives in travel, healthcare, federal, and technology sectors, with a focus on large-scale modernization and compliance.

How can I engage Jack for a project?

Contact Jack directly via phone, email, or LinkedIn, or schedule a call for an initial consultation.

Where can I learn more about platform features?

Visit the Features or Documentation pages for detailed information on platform capabilities and technical documentation.