Provide fractional CIO/CISO leadership for growth-stage, healthcare, regulated, and acquisition-driven organizations. Advise executives on technology strategy, cybersecurity, Microsoft 365/Azure modernization, data governance, vendor risk, AI-enabled automation, and post-acquisition integration. • Advise healthcare provider-services organizations on HIPAA/PHI safeguards, EHR operations, vendor risk, BAAs, Microsoft cloud controls, reporting, and security governance. • Guide Microsoft 365, Azure, Entra ID, Intune, Conditional Access, DLP, Power Platform, Power BI, and Microsoft Fabric modernization efforts. • Support post-acquisition technology integration, including platform rationalization, vendor consolidation, identity/security alignment, and operating model improvement. • Design AI-enabled workflows and prototypes using Claude, OpenAI APIs, databases, CRM platforms, and operational systems to improve customer-facing and internal processes. • Support customer security reviews, compliance evidence, vendor assessments, executive decision-making, and practical build-versus-buy technology recommendations. • Advise privately held, growth-stage, and regulated organizations on cybersecurity strategy, Microsoft 365/Azure security, Entra ID, Intune, Conditional Access, PIM, DLP, retention, eDiscovery, endpoint security, vendor risk, licensing, cloud security, and compliance readiness. • Provide fractional CIO/CISO leadership for healthcare provider-services clients, including HIPAA/PHI safeguards, EMR/EHR data governance, BAAs, security questionnaires, vendor risk reviews, executive reporting, and Microsoft cloud/security modernization. • Implemented Microsoft Copilot governance and adoption for healthcare clients, advising on AI licensing, data protection, DLP, identity controls, secure usage, and responsible adoption across business workflows. • Support customer security reviews and evidence packages by coordinating security controls, policies, access governance, data protection, and compliance documentation across SaaS and Microsoft cloud environments. • Negotiate technology renewals and vendor agreements, producing approximately 20% telecom savings and 10%+ software renewal savings while improving service accountability and security alignment.