Sherwood Callaway is an engineering leader and post-exit startup founder. Currently, he is the first engineering manager at 11x, where he leads development on Alice, the AI SDR. Previously, Sherwood co-founded Opkit, a healthcare SaaS company that launched five products, including one of the first-ever AI phone calling services, before being acquired by 11x in 2024. At Brex, he was the second infrastructure engineer, where he built the systems that supported Brex during hypergrowth.