Sherwood Callaway

Sherwood Callaway is the first Engineering Manager and Tech Lead at 11x, an AI sales technology company based in San Francisco, California. He joined the firm in 2024 following its acquisition of Opkit, a Y Combinator-backed healthcare software startup where he served as Co-founder and developed early AI phone calling services. In his current role, Callaway leads the development of Alice, an autonomous AI sales development representative that manages over one million prospect interactions monthly across more than 300 enterprise customers. Under his technical leadership, the Alice product scaled from its initial prototype to generate eight figures in annual recurring revenue. Previously, he worked as the second infrastructure engineer at Brex, scaling the financial technology company's production systems during hypergrowth. Callaway's career focuses on engineering leadership and scaling artificial intelligence products from early-stage development to enterprise deployment.