Fundraising Fox
Sherwood Callaway
InvestorFounderFounder at Sazabi · Founder at Opkit
San Francisco, California, United States
FoundedOpkit · YCSazabi · YC
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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 SazabiYC X26
Intro paths
YC
Sherwood went through Y Combinator (Spring 2026) — any YC alum in your network can reach them through the YC community.
GP
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 · 7
Co-founders at Sazabi
AA
Abhi Aiyer
Founder at OpkitYC S21
Intro paths
YC
Sherwood went through Y Combinator (Summer 2021) — any YC alum in your network can reach them through the YC community.
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In turn, Sherwood can intro founders to Opkit's investors below.
Opkit's investors · 7
Andreessen HorowitzMenlo Park · $500K – $50M checksCambrian VenturesSan Francisco · $300K – $1M checksGlobal Founders CapitalBerlin · $1M checks · since 2023MischiefSan Francisco · $1M – $5M checks · since 2023Socially FinancedChatham · $100K – $250K checks · since 2023Twenty Two VenturesPalo Alto · $50K – $250K checksY CombinatorSan Francisco · $500K checks · since 2021
Co-founders at Opkit
JK
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.
Investments
Per curated public sources.
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 Founder of Opkit and Founder at Sazabi.
- What companies did Sherwood Callaway found?
- Sherwood Callaway founded Opkit, Sazabi.
- What companies has Sherwood Callaway invested in?
- Investments tracked here include Ardent, Superset.
- 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).
Founder mafias
Y Combinator mafia10,603
Also came through, then founded or led a company.
Sam AltmanPresidentFounded Tools for Humanity +3Garry TanPresident and CEOFounded Posterous +2Jessica LivingstonFounder, RetiredFounded Y CombinatorAlexis OhanianPartnerFounded The Offseason +2Fred EhrsamYC Summer 2012Founded Nudge +1Matt HuangYC Winter 2015Founded Avarra Enterprise Avatar and AI-simulation +3
Andreessen Horowitz mafia93
Also came through, then founded or led a company.
Ben HorowitzInvestingFounded OpswareChris DixonGeneral Partner; Founder of a16z cryptoFounded a16z Speedrun +1Balaji SrinivasanBoard PartnerFounded Counsyl +1Erik TorenbergPartnerFounded VillageglobalJosh MerrillDesign Engineer FellowFounded Confirm +3Surojit ChatterjeeExecutive in ResidenceFounded Ema +2
Brex mafia51
Also came through, then founded or led a company.
Henrique DubugrasFounderFounded StoneRitik MalhotraDirector, Product ManagementFounded Savvy +2Roli SaxenaChief Customer OfficerFounded LinkedIn +1Tanooj LuthraEngineering Manager, Brex CashFounded Elph +1Cullen WilsonProduct Design LeadFounded WP Engine +1Keenan D. WilliamsRelationship ManagerFounded Rezi +1
Brex mafia50
Also came through, then founded or led a company.
Henrique DubugrasFounder and ChairmanFounded Stone +1Pedro FranceschiFounder and CEOFounded BrexRitik MalhotraDirector, Product ManagementFounded Savvy +2Carmen CollynsChief of Staff to the CEO, VP, Head of CommunicationsFounded Zuora +1Roli SaxenaChief Customer OfficerFounded LinkedIn +1Tanooj LuthraHead of Engineering for Startups + BankingFounded Elph +1
Davidson College mafia30
Also came through, then founded or led a company.
Same school
Also attended Y Combinator2,000
Tarek MansourCo-founder & CEO of KalshiSuhail DoshiFounder of Mixpanel; founder of ParticleSubomi OluwalanaCo-founder & CEO of ConvoyArhaan A.Deeptech Fellow at Clear VenturesCollin WallaceGeneral Partner at Lobby CapitalVictor SantosVictor Scout at One Way Ventures
+ 1,994 more
Also attended Davidson College103
Steve TregayManaging General Partner at Mission BiocapitalKaty MorrisAssociate, Investor Relations at JMI EquityDaniel HanksManaging Partner at Lavrock VenturesGray RobinsonPartner at Congruent VenturesJon BassettManaging Partner at NextGen Venture PartnersAnthony FoxxAdvisor at Autotech Ventures
+ 97 more
Also attended Dev Bootcamp12
Elsha Eliasa KweeCountry Director of Indonesia at Genesia VenturesRex SalisburySolo-GP at Cambrian VenturesBradley HarrisAngel at A-Frame Venture StudioJeffrey ChangInvestor at HotmailDavid J. PhillipsAngelCordelia PetersAssociate / Private Equity at Blue Earth Capital AG
+ 6 more
Also attended McIntire Business Institute at the University of Virginia3
Shared employers
Also worked at Sazabi5
Also worked at 11x9
Philipp WernerPartner at Project AMila CramerPrincipal at Project ATirso Martin SanchezInvestor at La FamigliaJustin KoFounder at OpkitHemant PhalakFounder at EntvinJames StirratCEO at Build
+ 3 more
Also worked at Opkit1
Also worked at Brex71
Henrique DubugrasCo-founder & former chairman of BrexPedro FranceschiCo-founder & CEO of BrexKatie BiberChief Operating Officer at ParadigmAyesha AroraVenture Partner at S32Matt MocharyInvestor at Fortius VenturesCarmen CollynsHead of Investor Relations at CAVU Consumer Partners
+ 65 more