Building Alice’s Brain: an AI Sales Rep that Learns Like a Human - Sherwood & Satwik, 11x

AI agents are becoming essential tools for teams of all sizes and industries - but training them to become experts in your product, business, and customerbase remains a challenge. What if onboarding a digital worker was as simple as uploading your pitch deck? At 11x, we built Alice, an AI SDR that writes outbound emails with the nuance and context of a top-performing human sales rep - because she learns like one too! In this talk, we'll share how we built a knowledge base that allows 11x customers to "train" Alice on their internal materials: PDFs, websites, call recordings, and more. We'll talk through the ingestion pipeline in detail, discuss storage/retrieval technologies and their tradeoffs, and explain how Alice uses the knowledge base to drive high-performance email outreach at scale. About Sherwood Callaway Sherwood Callaway is an emerging leader in the world of AI startups and AI product development. He currently serves as the first engineering manager at 11x, a series B AI startup backed by Benchmark and Andreessen Horowitz, where he oversees technical work on "Alice", an AI sales rep that outperforms top human SDRs. Alice is an advanced agentic AI working in production and at scale. Under Sherwood’s leadership, the system grew from initial prototype to handling over 1 million prospect interactions per month across 300+ customers, leveraging partnerships with OpenAI, Anthropic, and LangChain while maintaining consistent performance and reliability. Alice is now generating eight figures in ARR. Sherwood joined 11x in 2024 through the acquisition of his YC-backed startup, Opkit, where he built and commercialized one of the first-ever AI phone calling solutions for a specific industry vertical (healthcare). Prior to Opkit, he was the second infrastructure engineer at Brex, where he designed, built, and scaled the production infrastructure that supported Brex’s application and engineering org through hypergrowth. He currently lives in San Francisco, CA. A