Keith Wine

keith@thewines.usI am a senior executive and transformation leader with 35+ years of experience delivering large-scale operational, technology, and organizational change across federal and state government and global enterprises. My work has focused on leading complex, high-visibility programs in highly regulated environments—driving measurable outcomes across transportation, health and human services, higher education, and enterprise IT. I am actively leveraging analytics using Power BI and AI tools, including ChatGPT, Microsoft Copilot, Claude, and Perplexity, for advanced long-term strategic planning, deployment, and decisioning.  I have led initiatives impacting more than 100,000 users and managed multi-billion-dollar portfolios, including enterprise modernization efforts for the United States Postal Service, national transportation systems, and Medicaid Enterprise System transformations across multiple states. As Chief Administrative Officer and senior executive within a $6B public sector portfolio at ACS (a Xerox company), I oversaw service delivery, operational performance, and governance across IT outsourcing, business process outsourcing, and large-scale system modernization programs. In addition to my corporate leadership experience, I founded and successfully exited two companies, scaling operations to more than 3,900 employees—bringing an entrepreneurial, results-oriented approach to growth, efficiency, and innovation. I have also served multiple times as Chief of Staff to global executives, advising on strategy, transformation, and execution across complex organizations. Areas of Focus: • Enterprise Transformation & Digital Modernization • Public Sector Strategy & Government Operations • PMO Leadership & Large-Scale Program Execution • ERP, HHS & Transportation Systems • Data, Performance Analytics, AI & Operational Excellence • M&A Integration & Organizational Scaling Board & Advisory Interests: I am particularly interested in board and advisory roles where I can contribute to governance, transformation strategy, operational performance, and large-scale modernization initiatives.