Sherwood Callaway

Sherwood Callaway is a serial entrepreneur with a strong background in AI and FinTech. He co-founded Opkit, an AI-driven healthcare startup that automated phone calls for insurance verification and patient intake, which was acquired by 11x. His experience includes successfully bringing an AI product from concept to commercialization and exit. sessionize+3

He possesses deep expertise in building scalable infrastructure and AI agents. As an early infrastructure engineer at Brex, he was instrumental in scaling their production infrastructure. At 11x, he leads the technical development of 'Alice,' an AI sales rep that handles over 1 million prospect interactions monthly and generates significant revenue, showcasing his ability to lead and deliver high-impact AI solutions. sessionize+2

Sherwood is recognized as an emerging leader in AI startups and product development, with a focus on AI agents and observability. He actively shares his knowledge through speaking engagements, such as those on "AI Agent Development Tradeoffs" and "Observability in the AI Era." sessionize

He is currently an Infra Scout at Andreessen Horowitz (a16z), indicating his involvement and influence within the venture capital and tech investment landscape, particularly in infrastructure and developer tools. luma