Sherwood Callaway

Sherwood Callaway is founder and CEO of Sazabi, an AI-native observability company in Y Combinator's Spring 2026 batch. A second-time YC founder, he previously helped start infrastructure and observability work at Brex and earlier founded Opkit. Sazabi's pitch is that modern teams can send logs and let agents turn those events into investigations, alerts, and fixes without wiring a full metrics-and-traces stack first.

Brex, Opkit, and a second YC run

Callaway's public bio ties Sazabi directly to years spent building observability for fast-moving startups. He went through YC before with Opkit (S21), alongside founding engineer Justin Ko, and has said the new company is a return to the reliability problems he lived with at Brex. In a SiliconANGLE interview he framed the product as what Datadog-style tools might look like if they were designed around agents from day one.

Logs are all you need

Sazabi's core claim is that logs are enough once language models can read them at scale. "Fundamentally, logs are just events, metrics are aggregated events and traces are basically correlated events," Callaway told SiliconANGLE. "We only accept logs, and we create metrics and traces from those logs on the back end." He has called logs "the Occam's razor of observability" and described a background agent that looks for anomalies, investigates them, and decides whether they deserve a human's attention.

On agents that remember incidents

Where older tools restart every investigation from a blank dashboard, Callaway argues Sazabi should accumulate memory of a codebase, traffic patterns, and past incidents. The company is still early (closed alpha on its YC page, with angel backing from builders at other AI tools), and the watch reason is the claim that observability for AI-native teams is a new stack, not a chatbot bolted onto 2010-era monitoring.