Enterprise AI & Digital Transformation Consultant

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Summary

This Enterprise AI & Digital Transformation Consultant is a Transformational CIO/CTO/CAIO with over 25 years of driving measurable business outcomes through technology and a hands-on practitioner, not just an advocate, of AI and automation. Personally, uses ChatGPT (OpenAI), Claude (Anthropic), and Gemini (Google) daily for strategy development, prompt engineering, custom GPT workflow automation, research, and executive communications. At LuLaRoe, this Enterprise AI & Digital Transformation Consultant built the technology organization through $2.3B in peak annual revenue, designed platforms that handled over $1B in annual wholesale transactions, and generated $2B in total B2B/B2C marketplace revenue. Currently working as a Fractional CITO/CAIO through 5VIRTUES LLC, created and implemented a proprietary 90-Day AI Council framework to guide enterprise AI adoption across people, process, and technology; developed repeatable AI playbooks that clients now operate independently; and helped organizations select and deploy AI tools from RFP to trained teams. This Enterprise AI & Digital Transformation Consultant consistently delivers 25%+ productivity gains and measurable ROI within the first quarter. Expert in AI strategy, governance frameworks, vendor evaluation, prompt engineering, and practical AI automation that cuts operational costs and scales business capacity. 

Highlights

• AI Strategy, Transformation & Governance 

• eCommerce Platform Architecture 

• Cloud Infrastructure (AWS / Azure) 

• Digital Transformation & P&L Ownership 

• ERP / CRM / HCM Implementation

• Cybersecurity & SOC 2 Compliance 

• Prompt Engineering & GPT Workflows 

• Board-Level Reporting & Executive Communication 

• Global Team Leadership

Relevant Accomplishments

• Led eCommerce platform modernization from legacy system to WordPress (WooCommerce) and Shopify, coordinated external development agency, internal stakeholders, and third-party integrations, delivering a 15% conversion rate improvement and $37.5M in incremental annual revenue with full payback inside 90 days. 

• Deployed AI-assisted business intelligence tools providing real-time operational analytics, automated break-even reporting, and marketing performance dashboards previously built manually, driving a 20% improvement in marketing ROI. 

• Executed technology stabilization initiative, cutting system downtime by 75% and recovering an estimated $1.2M annually in lost productivity; personally managed vendor remediation across network, server, and hosting infrastructure. 

• Restructured the technology organization, hired key leadership, defined accountability structure, and improved project delivery speed by 40% while raising team engagement scores by 35%. 

• Integrated WMS (Pick Pack) systems across three distribution centers, reduced fulfillment errors by 30%, and improved average delivery times by two days. 

• Led enterprise-wide digital transformation on AWS/Azure, scaling the company to $2.3B in peak annual revenue, and architected systems processing $1B+ in annual wholesale transactions at 99.9% uptime with zero unplanned outages. 

• Launched B2B/B2C eCommerce marketplace serving 10,000+ independent retailers, generating $2B in cumulative revenue over five years, personally led platform architecture decisions, vendor selection, and go-live program management.

• Ran the de facto PMO across concurrent Oracle NetSuite ERP (from QuickBooks), Salesforce CRM, and Paycom HCM implementations, owned master program plan, cross-platform dependency management, vendor contracts, data migration, and UAT governance; reduced operational costs by 35% and improved data accuracy to 95%. 

• Led AI and automation readiness initiatives, evaluated emerging automation and analytics platforms (DOMO), implemented data pipeline automation, and laid the operational data foundation that enabled subsequent BI and predictive analytics investments. 

• Built and led a 30-person cross-functional IT team using OKRs and Agile, maintained 90% on-time delivery rate across a $100M+ technology portfolio. 

• Implemented enterprise cybersecurity program, achieving zero security breaches over eight years at $1B+ revenue scale, managed vendor selection, endpoint security, network segmentation, and compliance frameworks.  

• Managed Movex / Infor ERP rollout across manufacturing, sales, finance, and distribution, owned cross-functional coordination, vendor management, data migration, and UAT; improved operational efficiency by 25%. 

• Led global MPLS network transformation across 25 international locations, reduced annual network operating costs by 40% ($2M+ in savings) while improving reliability. 

• Designed virtual POS infrastructure enabling 25 new store openings, generating $50M in incremental retail revenue; launched first Magento eCommerce platform, generating $20M in online revenue within two years. 
• Built and maintained DR / Business Continuity program with colocation failover, delivered 99.95% system availability and zero data loss over 10 years. 

Roles

• Independent CTO / CIO Consulting 

• CIO 

• CTO 

• VP of Information Technology 

• Director & Manager, Network Operations 

• Infrastructure Analyst 

Request Expert / Similar Expert

Click “request expert” for a free initial screening call with this expert or a similar expert regarding your expert consulting needs