2x founder

Sherwood Callaway

Founder @ Sazabi ◆ DevOps/Infra/o11y ◆ Early Eng @ Brex ◆ 2x @ Y Combinator

Founder

Opkit· Summer 2021 🇺🇸 San Francisco, California, United States

in LinkedIn 𝕏 @shcallaway

2025Founder· Sazabi

Founder · since 2021

Company

Sazabi

Role

Founder & CEO

current

Stage

—

no public source

Raised

—

no public source

Based

San Francisco Bay Area

current

Founder / co-founder — the company's markEmployee / research role

Source: LinkedIn work history

Profile coverage5 of 7 · missing posts, contact

Opkit

AI phone calls for the US healthcare industry

Summer 2021

Experience

Career

Sazabi
Founder
Founder & CEO · San Francisco Bay Area · 2025 – Present
2025
Andreessen Horowitz
Infra Scout · San Francisco Bay Area · 2025 – Present
2025
11x
Tech Lead & Engineering Manager, Alice · San Francisco Bay Area · 2024 – 2025
2024
Opkit
Co-founder
Co-Founder & CEO · New York, United States · 2021 – 2024
2021
Brex
Software Engineer, Product (Bill Pay) · New York, New York, United States · 2020 – 2021
2020
Brex
Software Engineer, Infra (Observability) · New York, New York, United States · 2019 – 2020
2019
Brex
3rd Infra Engineer · San Francisco, California · 2019
2019
Crunchbase
Software Engineer, DevOps & Infra · San Francisco, California · 2017 – 2019
2017
CapTech Ventures, Inc
Software Developer · Charlotte, North Carolina Area · 2016
2016
CapTech Ventures, Inc
Software Developer Intern · Richmond, Virginia Area · 2015
2015

Bio

Sherwood Callaway is a 2x YC founder and software engineer with over ten years of experience in infrastructure, DevOps, and observability engineering roles top VC-backed startups, including Crunchbase and Brex. Currently, he is founder and CEO at Sazabi, the AI-native observability platform for fast-moving engineering teams. Sazabi is directly inspired by Sherwood's experience at Brex, where helped start the company's infrastructure and observability engineering teams.