Sherwood Callaway
InvestorFounderInfra Scout at Andreessen Horowitz · Founder at Sazabi · Co-founder/CEO at Opkit
San Francisco, California, United States
FoundedOpkit · YCSazabi · YCSazabi
Find your path to Sherwood
2,590 people in our graph share verified history with Sherwood — schools, employers, funds. One of them is your warm intro.
Erin Price-WrightunlockedSherwood: together at Andreessen Horowitz (2025–2026)
Sherwood: together at Andreessen Horowitz
×9Sherwood: together at Y Combinator
Sherwood: together at CapTech Ventures, Inc
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 · 4
Co-founders at Sazabi
AA
Abhi Aiyer
Co-founder/CEO 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 · 4
Co-founders at Opkit
JK
Justin KoFounder
Founder at Sazabi
Intro paths
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In turn, Sherwood can intro founders to Sazabi's investors below.
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.
Colleagues at Andreessen Horowitz
Adam Alpert
Founder at Pangea.app
Aditya Mehta
Founder at Suggestr
Aiden Slavin
Policy at a16z crypto
Alex Immerman
Partner at Andreessen Horowitz
Alex Rampell
General Partner at Andreessen Horowitz
Ali Yahya
General Partner at a16z crypto
Alisha Litman
Events at a16z crypto
Andrew Chen
General Partner at Andreessen Horowitz
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 Infra Scout at Andreessen Horowitz and Founder at Sazabi and Founder at Sazabi.
- What companies did Sherwood Callaway found?
- Sherwood Callaway founded Opkit, Sazabi, 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).
Founder mafias
Y Combinator mafia10,230
Also came through, then founded or led a company.
Sam AltmanPresidentFounded Tools for Humanity +3Garry TanPresident & CEOFounded Y Combinator +1Jessica LivingstonCo-founderFounded Y CombinatorAlexis OhanianPartnerFounded RedditFred EhrsamYC Summer 2012Founded Nudge +1Matt HuangYC Winter 2011Founded Paradigm +1
+ 10,223 more
Andreessen Horowitz mafia68
Also came through, then founded or led a company.
Marc AndreessenCo-founder & General PartnerFounded OpswareBen HorowitzCo-founder & General PartnerFounded OpswareChris DixonGeneral Partner; Founder of a16z cryptoFounded Founder CollectiveBalaji SrinivasanGeneral PartnerFounded Counsyl +1Erik TorenbergGeneral PartnerFounded VillageglobalSurojit ChatterjeeExecutive in ResidenceFounded Ema +1
+ 61 more
Brex mafia48
Also came through, then founded or led a company.
Henrique DubugrasCo-CEOFounded StoneRitik MalhotraDirector, Product ManagementFounded Savvy +2Tanooj LuthraSenior Engineering Manager, Foundation Platform + ObservabilityFounded Elph +1Cullen WilsonProduct Design LeadFounded WP Engine +1Keenan D. WilliamsRelationship ManagerFounded Rezi +1Asa MillerDesign EngineerFounded Pre +1
+ 41 more
Davidson College mafia14
Also came through, then founded or led a company.
Cameron HardestyB.A.Founded Your Poppy +2William WinkenwerderBSFounded CureatrTodd ThomsonBAFounded Dynasty Financial PartnersRex SalisburyBAFounded CambrianChris TrinettiBachelor of Science (BS)Founded MilkeninstituteAndrew AshurBachelor’s DegreeFounded Lucid Bots
+ 7 more
Dev Bootcamp mafia7
Also came through, then founded or led a company.
Jeffrey ChangRuby on RailsFounded Doblet +1David J. PhillipsSoftware Development - Cohort 0Founded Fondo +1Felix LobkowiczFull Stack Web Development (Ruby on Rails and Javascript)Founded Thrivo Wealth +1Rex SalisburyFounded CambrianChapman SnowdenFounded GoBuild (fka Brick)Alyssa RavasioWeb DevelopmentFounded Hipcamp
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 College92
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
+ 86 more
Also attended Dev Bootcamp12
Elsha E. 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 11x8
Philipp WernerPartner at Project AMila CramerPrincipal at Project AJustin KoFounder at OpkitHemant PhalakFounder at EntvinJames StirratCEO at BuildHasan SukkarFounder and Non-Executive Chairman at 11x
+ 2 more
Also worked at Opkit1
Also worked at Brex65
Henrique DubugrasCo-founder & former chairman of BrexPedro FranceschiCo-founder & CEO of BrexKatie BiberChief Operating Officer at ParadigmMatt MocharyInvestor at Fortius VenturesCarmen CollynsHead of Investor Relations at CAVU Consumer PartnersHadley CallawaySoftware Engineer at Asymmetric Capital Partners
+ 59 more