Derrick Cash

AI Strategist | Government Modernization Leader | Servant Technologist

Vice President, Innovation & Delivery at RADcube  |  FormWave Collective

Derrick Cash is a transformational technology executive with over two decades of experience leading digital strategy, AI innovation, and organizational change across government, nonprofit, and private sectors. As Vice President of Innovation & Delivery at RADcube, he spearheads large-scale digital modernization and AI-driven transformation initiatives—serving public agencies, regulated industries, and mission-focused organizations throughout the Midwest and beyond.

Derrick’s journey began far from boardrooms and data centers. Raised in rural Indiana with limited access to technology, his early curiosities were shaped by books, biology, and blue-collar resilience. He later emerged as one of the region’s most respected digital leaders—proving that perseverance, service, and systems thinking can outperform privilege.

Derrick’s career includes a range of influential leadership roles across public and private sectors. He currently leads innovation strategy at RADcube, where he works closely with agency leaders and enterprise clients to embed AI, optimize delivery systems, and drive measurable results. Prior to this, he served as Deputy Chief Technology Officer for Indiana’s Family and Social Services Administration (FSSA), where he provided executive-level advisory, led statewide modernization programs, and managed high-stakes HHS digital initiatives. He previously served as FSSA’s Senior Manager of Enterprise Architecture, establishing governance and enterprise roadmaps across complex systems. Earlier in his career, Derrick founded and directed the Department of Informatics for the City of Westfield, Indiana, centralizing IT, GIS, and PMO operations during a period of explosive municipal growth. In the private sector, he rose through the ranks at Autobase, Inc., helping scale a CRM platform into a key revenue stream by leading database development and team leadership. In parallel to his professional career, Derrick continues to serve his community—currently as an elected member of the Cold Spring School Board, where he helps guide strategic planning and innovation in K–8 education.

Derrick’s dedication to strengthening business opportunities through strategic and sustainable technology planning, enterprise road mapping, systems management, process improvement, and delivery execution is built upon more than 20 years of blended technical and business experience. He holds a B.S. in Informatics from Indiana University, graduating in the top 2% of his class, and an MBA from Indiana Wesleyan University.

• AI Readiness Assessments & Responsible AI Strategy
• Digital Government Modernization
• Data Governance & Privacy-First Transformation
• PMO-as-a-Service (PMOaaS) and ISO-aligned operational frameworks
• AI-powered Product Innovation via RADLabs & Collective Intelligence models

A frequent speaker, strategist, and mentor, Derrick blends empathy and execution. He is known for shaping high-performing teams, building human-centered technology ecosystems, and bringing clarity to the complexity of digital change. His leadership philosophy is rooted in Jim Collins’ Level 5 Leadership—driven by humility, grit, and purpose.

When he’s not transforming institutions, Derrick is likely listening to an audiobook on team dynamics or hiking a state park trail—always thinking about how technology can be used as a tool for the common good.