Randi N. Gray

About Randi N. Gray

AI doesn’t replace leadership—it strengthens it when paired with the right systems.I help leaders build stronger systems by using AI practically, responsibly, and profitably—without hype, overwhelm, or unnecessary complexity.With 25+ years in corporate IT leadership, I\'ve seen firsthand how the right systems unlock extraordinary leadership potential. As the Head of IT for Merit Beauty, a global cosmetics brand, I oversee technology strategy, cybersecurity, and digital operations for 130+ employees across multiple regions. I\'ve led large-scale implementations, automated workflows, strengthened security posture, and delivered over $100K in annual cost savings—all while supporting fast-moving, people-centered teams.Now, through Stronger Systems Group, I help organizations and leaders do the same.WHAT I OFFER: Speaking EngagementsKeynotes, panels, and leadership talks on AI adoption, systems thinking, and leadership excellence for corporate conferences, industry events, and executive gatherings. Workshops & TrainingPractical, immediately actionable programs including-AI productivity workshops for teams and executives-Leadership workflow training and systems thinking-StrongHER Systems™ – My flagship leadership program for women navigating complex roles, high expectations, and competing demands ConsultingStrategic advisory for-AI integration and responsible adoption-Leadership systems design and optimization-Organizational transformation and change management-Executive coaching for clarity and confidence StrongHER Career SolutionsProfessional resume revision and career positioning services for leaders ready to articulate their value and advance to the next level.MY APPROACH:My work is grounded in real operational expertise, systems thinking, and a human-centered approach to technology. I help leaders move from experimentation to confident execution by building systems that support both performance and well-being.Core expertise:AI adoption & governance | Leadership systems design | Workflow automation | Strategic planning | Keynote speaking | Women\'s leadership development | Change management | IT strategy Let\'s work together:Interested in workshops, consulting, or speaking engagements? Send me a message with \"WORKSHOP\" or email i•••@strongersystemsgroup.com Learn more: strongersystemsgroup.com

Experience

1. Head of Information Technology

   MERIT

   Jul 2023 — Present · New York, NY, US

   Serve as the senior technology leader for a global, fast-growing beauty brand, overseeing IT strategy, cybersecurity, and digital operations for 130+ employees across multiple regions.Key impact-Led enterprise system implementations and workflow automation initiatives-Strengthened cybersecurity posture and governance frameworks-Designed scalable systems to support growth and cross-functional collaboration-Delivered over $100K in annual cost savings through vendor optimization and automation-Acted as a strategic advisor to executive leadership on technology-enabled decision-makingThis role directly informs my consulting work, providing hands-on experience applying systems thinking and AI-enabled solutions in real operating environments.Workflow Automation & ProductivityLed enterprise workflow automation initiatives across IT, operations, and cross-functional teams—reducing manual effort, improving handoffs, and enabling faster decision-making.Impact-Automated repeatable workflows across onboarding, access management, and vendor processes-Reduced operational friction for 130+ employees across multiple regions-Improved response times, consistency, and leadership visibility into workstreamsCost Optimization Through Systems ThinkingConducted a full audit of technology vendors, contracts, and usage patterns to align spend with business value.Impact-Delivered $100K+ in annual cost savings-Eliminated redundant tools while maintaining performance and security-Reinvested savings into scalable, higher-impact systemsExecutive Advisory & Decision SupportServed as a strategic technology advisor to executive leadership, translating complex technical concepts into clear options and tradeoffs.Impact-Supported leadership decision-making around growth, security, and scalability-Designed governance frameworks that balanced innovation with risk management-Built executive confidence in adopting new tools and systems

Education

• Teachers College, Columbia University

  Master of Arts - MA, Educational/Instructional Technology

• Binghamton University School of Management

  Bachelor of Science (B.S.), Management & Marketing

  1992 — 1996

Skills

• Os X
• Dns
• Databases
• Antivirus
• Sql Server
• Process Improvement
• Microsoft Sql Server
• Cross-Functional Team Leadership
• System Administration
• Application Support Management
• Troubleshooting
• Microsoft Office 2010
• Project Management
• Blackberry
• Security
• Citrix
• Routers
• Printers
• Software Installation
• Operating Systems
• Mobile Device Management
• Windows
• Software Documentation
• Office 2010
• Analysis
• Access
• Sharepoint
• Training
• Switches
• Program Management
• Group Policy
• Exchange Server 2010
• Tcp/Ip
• Remote Desktop
• Windows 7
• IT Management
• Dhcp
• Laptops
• Strategic Planning
• Microsoft Exchange