Sherwood Callaway

At-a-Glance

Serves as an Infra Scout at a16z.
Exited founder of Opkit, a YC-backed AI startup in medical billing.
Commercialized one of the first LLM-based voice agents at Opkit.
Led engineering for Alice at 11x, an AI agent sales rep sending over 50k emails per day.
Helped establish Infrastructure and Observability teams at Brex.
Spoken at AI conferences including LangChain Interrupt and AI Engineer World’s Fair.

Biography

Sherwood Callaway is a software developer with over a decade of experience at venture capital-backed startups. He is an exited YC founder, having started and successfully sold Opkit, an AI startup focused on medical billing. At Opkit, Callaway played a pivotal role in building and commercializing one of the first voice agents powered by large language models.