Where does Sherwood Callaway work?

Sherwood Callaway is Co-founder/CEO of Opkit and Founder at Sazabi.

What companies did Sherwood Callaway found?

Sherwood Callaway founded Opkit, Sazabi.

Where did Sherwood Callaway go to school?

Sherwood Callaway studied at Y Combinator (P26); Y Combinator (S21); Davidson College (Bachelor of Arts (B.A.), History).

Sherwood Callaway

Founder

Founder at Sazabi · Co-founder/CEO at Opkit

San Francisco, California, United States

FoundedOpkit · YC Sazabi · YC

About

Sherwood Callaway is a software engineer with over ten years of experience in infrastructure, DevOps, and observability engineering at VC-backed companies including Crunchbase and Brex. He is founder and CEO of Sazabi, an observability platform.

Founder at Sazabi YC X26

Intro paths

Sherwood went through Y Combinator (Spring 2026) — any YC alum in your network can reach them through the YC community.

Their group partner at YC was Aaron Epstein, General Partner at Y Combinator — the partner who ran Sazabi's batch and knows the company first-hand. YC profile ↗

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In turn, Sherwood can intro founders to Sazabi's investors below.

Sazabi's investors · 4

Orange CollectiveDanville Village GlobalCovina · $100K – $500K checks Y CombinatorSan Francisco · $500K checks · since 2026 Zypsy CapitalSan Francisco · $50K – $400K checks

Co-founders at Sazabi

Abhi Aiyer

Co-founder/CEO at Opkit YC S21

Intro paths

Sherwood went through Y Combinator (Summer 2021) — any YC alum in your network can reach them through the YC community.

→

In turn, Sherwood can intro founders to Opkit's investors below.

Opkit's investors · 4

Global Founders CapitalBerlin · $637K – $32M checks · since 2023 MischiefSan Francisco · $1M – $5M checks · since 2023 Socially FinancedChatham · $100K – $250K checks · since 2023 Y CombinatorSan Francisco · $500K checks · since 2021

Co-founders at Opkit

Justin KoFounder

Experience

SazabiFounder & CEOcurrent2025 — presentSan Francisco Bay Area
Andreessen HorowitzInfra Scoutcurrent2025 — presentSan Francisco Bay Area
11xTech Lead & Engineering Manager, Alice2024 — 2025San Francisco Bay Area
OpkitCo-Founder & CEO2021 — 2024New York, United States
BrexSoftware Engineer, Product (Bill Pay)2020 — 2021New York, New York, United States
BrexSoftware Engineer, Infra (Observability)2019 — 2020New York, New York, United States
Brex3rd Infra Engineer2019San Francisco, California
CrunchbaseSoftware Engineer, DevOps & Infra2017 — 2019San Francisco, California
CapTech Ventures, IncSoftware Developer2016Charlotte, North Carolina Area
CapTech Ventures, IncSoftware Developer Intern2015Richmond, Virginia Area

Skills & more

Angel Investing1Venture Capital1AI Agents1Networking1Cryptography1Computer Science1Databases3Computer Networking1Finance1Accounting1Cloud Computing1Communication1

+12 more

Data AnalysisAnalyticsManagementWeb DesignGraphic DesignFigma (Software)Facebook Ads ManagerFacebook AdsPublic SpeakingGoogle AdsOperating SystemsGoogle Cloud Platform (GCP)

Certified Kubernetes Administrator — Cloud Native Computing Foundation (CNCF)
AWS Certified Solutions Architect - Associate — Amazon Web Services (AWS)
Triplebyte-Certified Generalist Software Engineer — Triplebyte
Oracle Certified Associate Java SE 8 Programmer I — Oracle

From Sherwood's professional profile.

Frequently asked questions

Who is Sherwood Callaway?: Sherwood Callaway is a software engineer with over ten years of experience in infrastructure, DevOps, and observability engineering at VC-backed companies including Crunchbase and Brex. He is founder and CEO of Sazabi, an observability platform.
Where does Sherwood Callaway work?: Sherwood Callaway is Co-founder/CEO of Opkit and Founder at Sazabi.
What companies did Sherwood Callaway found?: Sherwood Callaway founded Opkit, Sazabi.
Where did Sherwood Callaway go to school?: Sherwood Callaway studied at Y Combinator (P26); Y Combinator (S21); Davidson College (Bachelor of Arts (B.A.), History).