Sherwood Callaway

Sherwood Callaway helped start the infrastructure and observability engineering teams at Brex, according to Sazabi's YC page. He is founder and CEO of Sazabi, an AI-native observability platform in Y Combinator's Spring 2026 batch.

Reliability Problems at Brex

Callaway has more than ten years of experience in infrastructure, DevOps and observability roles at VC-backed startups including Crunchbase and Brex. Sazabi is directly inspired by his time at Brex. His earlier ventures include phone call automation platform Opkit, according to SiliconANGLE.

Building Sazabi Around Logs

"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 called logs "the Occam's razor of observability."

Sazabi announced an $8 million seed round led by J2 Ventures, Village Global and Y Combinator, with participation from Orange Collective and more than 60 angel investors, according to its blog. Its stated vision is "self-healing software."