Build and Ship a Web App with Claude Code

Samuel J Cummings

VP of AI Engineering, GenAI works

Sam Cummings builds AI agents and the context systems that make them work in the real world. Sam leads AI Engineering at Gen AI Works, one of the world’s largest AI communities, where he helps builders, startups, and enterprise teams move from AI experiments into real products, workflows, and adoption. He is also building at the edge of agentic AI, with a focus on local-first systems, memory, orchestration, and computer use. His core belief is simple: agents rarely fail because the model is weak. They fail because the system does not understand the user, the work, the environment, or the constraints well enough to act with confidence. That context layer is what Sam teaches. Sam previously co-founded Dataplant, an AI-powered customer success platform acquired in 2026, and served as Head of Data Science at Gainsight, where he led a global team building predictive models for enterprise retention and growth. Across more than a decade of building, he has shipped systems across customer success, CRM, ERP, predictive analytics, and agentic workflows for 150+ companies. He has also interviewed 90+ leaders across the agentic AI space.