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A profile about the people, projects and experiences behind their work. Discover their career, contributions and connections.

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Company name

2022

Founder

Company name

2022

Founder

Profile name

A profile about the people, projects and experiences behind their work. Discover their career, contributions and connections.

CareerDetails being loaded

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Company name

2022

Founder

Company name

2022

Founder

Sherwood Callaway

Sherwood Callaway leads Sazabi, which builds an AI-native observability platform for engineering teams. He previously co-founded Opkit, which was acquired by 11x, where he helped rebuild the Alice sales agent; earlier, he built infrastructure and observability teams at Brex.

Career

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Based in: San Francisco
Elsewhere

Sazabi

Nov 2025 — Present

Founder and CEO

Andreessen Horowitz

Sep 2025 — Present

Infrastructure Scout

11x

Sep 2024 — Jun 2025

Tech Lead & Engineering Manager, Alice

Opkit

Jun 2021 — Nov 2024

Co-Founder and CEO

Brex

Software Engineer, Product (Bill Pay)
Oct 2020 — Jun 2021
New York City, New York, United States
Software Engineer, Infra (Observability)
Oct 2019 — Sep 2020
New York City, New York, United States
3rd Infra Engineer
Feb 2019 — Oct 2019
San Francisco, California, United States

Crunchbase

May 2017 — Feb 2019

Software Engineer, DevOps & Infra

CapTech

Software Developer
May 2016 — Dec 2016
Charlotte, North Carolina, United States
Software Developer Intern
May 2015 — Aug 2015
Richmond, Virginia, United States

Y Combinator

Bradfield School of Computer Science

Dev Bootcamp

McIntire Business Institute at the University of Virginia

Davidson College

Bachelor's studies in history

Products & media

blog.sherwoodcallaway.com

Round Two

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

Writing

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.

Writing

youtube.com

The End of Manual Debugging

A conversation about Sazabi’s AI-native approach to observability, his experience at Brex, and lessons from building startups.

Media appearance

youtube.com

Why Nobody Needs Metrics or Traces Anymore

Callaway discusses Sazabi’s vision for observability and how AI could change debugging and production reliability.

Media appearance

mastra.ai

Sazabi: AI-Native Observability for Fast-Moving Teams

A podcast conversation about Sazabi’s approach to logs, conversational debugging, and AI agents for monitoring.

Media appearance

siliconangle.com

Startup Sazabi bets on logs and AI agents to replace traditional observability stacks

Callaway explains Sazabi’s logs-first approach and how its AI agent analyzes production systems.

Media appearance

Software Engineer, Product (Bill Pay)

Software Engineer, Infra (Observability)

3rd Infra Engineer

Software Developer

Software Developer Intern

Products & media

Round Two

Observability’s past, present and future

The End of Manual Debugging

Why Nobody Needs Metrics or Traces Anymore

Sazabi: AI-Native Observability for Fast-Moving Teams

Startup Sazabi bets on logs and AI agents to replace traditional observability stacks

Curated Lists

List Inclusions

Software Engineer, Product (Bill Pay)

Software Engineer, Infra (Observability)

3rd Infra Engineer

Software Developer

Software Developer Intern

Products & media

Round Two

Observability’s past, present and future

The End of Manual Debugging

Why Nobody Needs Metrics or Traces Anymore

Sazabi: AI-Native Observability for Fast-Moving Teams

Startup Sazabi bets on logs and AI agents to replace traditional observability stacks

Curated Lists

List Inclusions