Fundraising Fox

Gillian OBrien

Founder

Founder at Cherry

United States

FoundedCherry Β· YC

About

Gillian O'Brien founded Cherry, a Y Combinator startup focused on employee benefits. After the company's shutdown, she served as Chief of Staff at Dover and later as Head of Startup Community at Pilot.com, before becoming General Manager at Remote. She also invests as a scout at CRV.

Founder at CherryYC W19

Intro paths

YC

Gillian went through Y Combinator (Winter 2019) β€” any YC alum in your network can reach them through the YC community.

β†’

In turn, Gillian can intro founders to Cherry's investors below.

Cherry's investors Β· 2

Fin CapitalSan Francisco Β· $250K – $15M checksY CombinatorSan Francisco Β· $500K checks Β· since 2019

Co-founders at Cherry

EOEmily OBrien
Emily OBrienFounder

Experience

  1. Leaders In TechFellowcurrent2025 β€” present
  2. RemoteHead of Product Marketing2025 β€” 2026
  3. RemoteGeneral Manager, Recruit Product2024 β€” 2026
  4. RemoteGeneral Manager2023 β€” 2026
  5. 500 GlobalStartup Mentor2023 β€” 2025
  6. CRVVenture Scout2023 β€” 2025San Francisco Bay Area
  7. Pilot.comFounder in Residence / Head of Startup Ecosystem2022 β€” 2023
  8. DoverChief Of Staff2020 β€” 2022San Francisco, California, United States
  9. Cherry (YC 19)Co-Founder, CEO2018 β€” 2020San Francisco Bay Area
  10. TerezManager of Social Media & Influencer Marketing2018New York, New York, United States

Skills & more

Product Development1Business StrategyMarketing StrategyProduct MarketingStrategic CommunicationsPositioning (Marketing)Product LaunchRecruiting2Artificial Intelligence (AI)2Strategy27Entrepreneurship15Product Management3
+12 moreRemote WorkLong-term VisionExecutive RelationshipsAsyncLeadershipHiringSalesPublic SpeakingInterpersonal SkillsCommunicationTeamworkManagement
  • Registered Yoga Teacher, 200-Hour (RYT-200) β€” Yogaworks

From Gillian's professional profile.

Frequently asked questions

Who is Gillian OBrien?
Gillian O'Brien founded Cherry, a Y Combinator startup focused on employee benefits. After the company's shutdown, she served as Chief of Staff at Dover and later as Head of Startup Community at Pilot.com, before becoming General Manager at Remote. She also invests as a scout at CRV.
Where does Gillian OBrien work?
Gillian OBrien is Founder of Cherry.
What companies did Gillian OBrien found?
Gillian OBrien founded Cherry.
Where did Gillian OBrien go to school?
Gillian OBrien studied at Y Combinator; Leaders In Tech; New York University (Bachelor's degree).

Founder mafias

Y Combinator mafia8,773

Also came through, then founded or led a company.

Sam AltmanPresidentFounded Tools for Humanity +3Jessica LivingstonCo-founderFounded Y CombinatorAlexis OhanianYC Summer 2005Founded RedditFred EhrsamYC Summer 2012Founded Nudge +1Matt HuangYC Winter 2011Founded HotspotsTrae StephensYC Winter 2022Founded Pursuit +1

+ 8,766 more

Y Combinator mafia4,716

Also came through, then founded or led a company.

Ryan SheaEntrepreneurshipFounded StacksTarek MansourFounded KalshiSuhail DoshiEating beans & riceFounded Playground +1Subomi OluwalanaW22Founded ConvoyDarius "Bubs" MonsefS19Founded Sightbox +3Matthew ScholzFounded Oisin Biotechnologies +3

+ 4,709 more

New York University mafia86

Also came through, then founded or led a company.

Jonathan RossHonors Mathematics and Honors Computer ScienceFounded GroqRajiv KhemaniMSFounded Auradine +3Ben ZisesReal Estate Finance and InvestmentFounded Superangelsyndicate +2Uri LopatinResidencyFounded Pardes Biosciences +1Robby YungM.A.Founded The Sandbox +1Ivan KiriginBAFounded YesGraph +1

+ 79 more

500 Global mafia67

Also came through, then founded or led a company.

Melanie Perkins500 Global 2012Founded CanvaCliff Obrecht500 Global 2012Founded CanvaCameron Adams500 Global 2012Founded CanvaEoghan McCabeGA 3 2011Founded FinDes TraynorGA 3 2011Founded FinHarry GrunerGA 19Founded Hilos +2

+ 60 more

Leaders In Tech mafia26

Also came through, then founded or led a company.

Sam HashemiFounded Felt +1Michael BabineauFellow (2022-2023)Founded Second Measure +1Michael HeinrichFounded OG Labs +1Ferhat BabacanFellowFounded Bluedot +1Chase AdamBoard MemberFounded WatsiArturo ElizondoFellowFounded The Every Company

+ 19 more

Same school

Also attended Y Combinator2,000

Tarek MansourCo-founder & CEO of KalshiSuhail DoshiFounder of Mixpanel; founder of ParticleSubomi OluwalanaCo-founder & CEO of ConvoyMaroof AhmedFounder at Octopus VenturesJustin SwartPartner at Bitkraft Esports VenturesCollin WallaceGeneral Partner at Lobby Capital

+ 1,994 more

Also attended Leaders In Tech21

Nick FitzInvestor at Juniper Ventures Management, LlcJoe GreensteinPartner at Very Serious VenturesCameron PeakePartner at Restive VenturesMaria AlegreManaging Partner at Flori VenturesJason TanFounder/CEO at SiftGareth MacLeodFounder/CEO at Tinker

+ 15 more

Also attended New York University385

Jonathan RossFounder of Groq; inventor of Google's TPU β€” now at NvidiaGabriella GiglioHR & Executive Talent at General CatalystAndrea EchstenkamperVP of Marketing at HeavybitRami BranitzkyPartner at Sapphire VenturesZach WhiteInvestment Team at 8VCAnkita TiwariPrograms Manager at StartX

+ 379 more

Shared employers

Also worked at Leaders In Tech11

Joe GreensteinPartner at Very Serious VenturesChase AdamPartner at Very Serious VenturesArturo ElizondoAdvisor at AvilaSam YaganCo-Founder and Managing Director at Corazon CapitalDina BurkitbayevaCo-Founder at PsyMed VenturesMada SegheteCo-Founder & CEO, Upside at xfactor ventures

+ 5 more

Also worked at Remote13

Job van der VoortCo-founder & CEO of RemoteNiko BonatsosVerdict Capital founder and pre-consensus investor formerly at General CatalystHannah SealInvestor at Index VenturesJan HammerInvestor at Index VenturesIsaiah Baril-DoreInvestor at Index VenturesKarly WentzPartner at B4 Capital

+ 7 more

Also worked at 500 Global145

Kaz TeradaVenture Advisor at Monta Vista CapitalChristal NgAssociate at Golden Gate VenturesDemi ObayomiPrincipal at Sapphire VenturesGbenga AjayiPartner, Head of Africa and Middle East at QED InvestorsJustin LedbetterChief Operating Officer, Marlan Space at Cortado VenturesJessica KohSenior Executive Director, Investment at Vertex Ventures Sea Management Pte. Ltd.

+ 139 more

Also worked at CRV55

Ann Miura-KoCo-founding Partner at FloodgateBruce SachsInvestor at CRV (Charles River Ventures)Rick BurnesInvestor at CRV (Charles River Ventures)Erica VanInvestment Director at Intel CapitalSanto PolitiInvestor at Spark CapitalAnnie KadavyVenture Partner at Redpoint Ventures

+ 49 more