Sherwood Callaway founded and leads Sazabi, an AI observability platform for engineering teams. He previously cofounded Opkit, which was acquired by 11x, where he helped rebuild the Alice sales agent. Earlier, he built infrastructure and observability teams at Brex and worked at Crunchbase.

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Sherwood Callaway founded and leads Sazabi, an AI observability platform for engineering teams. He previously cofounded Opkit, which was acquired by 11x, where he helped rebuild the Alice sales agent. Earlier, he built infrastructure and observability teams at Brex and worked at Crunchbase.

Career

Founder and CEO at Sazabi until Present
blog.sherwoodcallaway.com

Round Two

A founder’s reflection on infrastructure engineering, building Opkit and returning to developer tools.

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blog.sherwoodcallaway.com

Observability’s past, present and future

Sherwood traces distributed tracing and observability practices, argues that interpretation remains the bottleneck, and considers the complexity created by AI-generated software.

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