Akin Olaoye

I founded and lead an AI transformation consulting practice helping ecommerce and retail businesses move from AI curiosity to practical, measurable adoption. My work spans the full engagement lifecycle, AI readiness assessments, workflow automation design, tool deployment (Microsoft Copilot, Claude AI, Power Automate), and change management for non-technical teams. What I focus on: - Deploying generative AI tools that reduce manual effort and free up business owners to focus on growth - Building prompt engineering playbooks and AI SOPs that teams can use independently - Designing AI-powered inventory forecasting and customer communication workflows - Translating AI strategy into prioritized roadmaps with clear ROI benchmarks Current client work includes an ecommerce eyewear retailer (House of Lunettes), where AI-enabled automation has reduced operational admin time by ~35%.

Led cloud modernization and AI-enabled automation across a multi-departmental state agency. Delivered Power Platform solutions improving workflow efficiency by 40%, including a Construction Document Management system using M365, Power Automate, and AI Builder for intelligent document classification. Managed full-lifecycle Microsoft cloud migration and led change management for 200+ users. Deployed Crash Data dashboard to cloud, enhancing data accessibility for 100+ users and cutting query times by 50%. Managed cross-functional teams in Power Platform and Salesforce implementations, delivering projects on time and under budget.

Oversaw enterprise migration of legacy systems to multi-cloud environments (Azure, AWS, GCP). a team of 7 TPMs delivering 35+ mission-critical initiatives. Deployed ServiceNow ITSM, Security, and Compliance modules globally. Reduced program costs by $450K through timeline acceleration and resource optimization

Served as RTE for a 60+ person Agile Release Train delivering M365 modernization and enterprise cybersecurity programs. Led Claims Adjudication optimization reducing processing errors by 25%. Improved on-time feature delivery by 30% through structured ART ceremonies via Jira Align. Deployed Microsoft Pilot across 6 Florida Blue Subsidiaries

Led CMS Interoperability Final Rule compliance program for Patient Access and Payer-to-Payer APIs. Secured 90/10 federal CMS funding through Advanced Planning Document (APD) development across a $45M+ combined project portfolio.

Supported the RFP Development for a bid to deliver a solution on a bid for Veridos and strategic partners Developed and defined the project management framework to meet the Request for Information from the customer Identified and recommended a resource management plan to define all needed skill sets required to meet customer expectations

Deployed enterprise-wide Multi-Factor Authentication across 400+ applications using Azure Active Directory and Splunk. Administered a $9.5M program budget across 8 concurrent security remediation initiatives. Delivered ITSM projects on schedule enabling full compliance with federal cybersecurity mandates.

Managed a $30M Technical Advisory Services contract for the State of Tennessee Medicare Transformation. Delivered the New Medicare Card Project and Medicaid LTSS integration impacting 1.4M+ beneficiaries. Coordinated population health management software rollout across 12 pilot hospitals. Project Management Office Lead for the KPMG TAS Engagement to manage framework deliverables. Engagement Manager – New Medicare Card Project – Advisory Tennessee State & Local. Created control memos/letters to increase resource needs for KPMG TAS support for Project Management services on the SSNRI project. Coordinated the high-level strategy approach for the DXC Territory Batch Query process for the MBD2 Data exchange approach with CMS and presented the recommendation to HCFA for approval. Created a detailed MS project schedule to identify high-level CMS milestones and workstream activities for MMIS, ACCENT, T-MSIS, and TEDS required to meet testing timelines and operational milestones.. Developed the Tennessee CMS IAPD document to obtain funding of $11.5 million to execute the New Medicare Card project and worked with HPE, TEDS, SPMO, IV&V & HCFA executives to determine resource needs, impacted systems, and define project governance mode. Oversight responsibilities for the Program Management office team to coordinate monthly budget reports, portfolio management, enterprise resource management and integrated master schedules

Led Phase I & II delivery of KYNECT, Kentucky's ACA-compliant Health Benefit Exchange platform — supporting 500K+ enrollees at launch. Managed multi-vendor integration of cloud-based Provider and Eligibility & Enrollment systems. Implemented IaaS failover infrastructure for the Kentucky State Health Benefits Administration. Served as a Project Manager on the CGI EPMO to deliver Technical and Business Solutions for the Kentucky State MMIS Led an Infrastructure workstream to implement a dedicated connectivity circuit and failover site leveraging IaaS cloud solution for the MMIS KYNECT Program Led the Maintenance & Operations team with 15 offshore and 32 onshore technical resources with a team strength to support KHBE systems

Project Manager Roles: Community Health Systems · HealthSpring/Cigna · Geisinger Health Plan · BlueCross BlueShield · Providence Health Systems Series of IT project manager roles across major health systems and payers. Notable projects: HIPAA compliance programs, data center migrations, SSO implementations, Cerner EHR deployments, ICD-9/10 conversions, and enterprise SharePoint rollouts.

Engineering Management