Fundraising Fox

Gillian OBrien

Founder

Founder at Cherry

United States

FoundedCherry · 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.

LinkedIn ↗X / Twitter ↗
Latest on 𝕏

gillian @gillianxobrien

On the downside I am sick and miserable, on the upside I know my voice is about to be tea

Jul 29, 2026 · ♥ 11

gillian @gillianxobrien

Yes I am watching widows bay.

Jul 29, 2026 · ♥ 4

gillian @gillianxobrien

I wanna visit a small town where everyone is referred to by their last name, the diner doesn’t serve espresso - only drip, and someone recently disappeared/got murdered/ or is haunted. Like is that too much to ask omg

Jul 29, 2026 · ♥ 35

Founder at CherryYC W19

Intro paths

YC

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

→

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

Cherry's investors · 2

Fin CapitalY Combinator

Co-founders at Cherry

EOEmily OBrien
Emily OBrienFounder

Experience

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

Education

  1. Y Combinator
  2. Leaders In Tech
  3. New York UniversityBachelor's degree2013 — 2017
  4. Walnut Hill School for the Arts2010 — 2013

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) — Yogaworks

From Gillian's professional profile.

Founder mafias

Y Combinator mafia8,668

Also came through, then founded or led a company.

Sam AltmanPresidentFounded LooptFred EhrsamYC Summer 2012Founded CoinbaseMatt HuangYC Winter 2011Founded HotspotsTrae StephensYC Winter 2022Founded PursuitDelian AsparouhovYC Summer 2014Founded Nightingale +1Justin KanYC Winter 2018Founded Rye +3

+ 8,661 more

New York University mafia65

Also came through, then founded or led a company.

Ivan KiriginBAFounded YesGraph +1Juan MedinaMaster of Science (MS)Founded Isabl +1Michael MonteroBAFounded CrowdTwistRobby YungM.A.Founded Animoca BrandsRajiv KhemaniMSFounded Upscale AICamron BlackburnBachelor’s DegreeFounded E14Fund

+ 58 more

Leaders In Tech mafia17

Also came through, then founded or led a company.

Sam HashemiFounded Felt +1Jason TanFounded SiftGareth MacLeodConnecting with peopleFounded TinkerIba MasoodFounded Tara AIMichael BabineauFellow (2022-2023)Founded Second MeasurePanpan WangFounded The Flex Company

+ 10 more

Dover mafia4

Also came through, then founded or led a company.

Akash SharmaBusiness Operations LeadFounded VellumSidd SeethepalliFounding EngineerFounded VellumNoa FlahertySoftware Engineering ManagerFounded Vellum

Same school

Also attended Y Combinator2,000

Leo LuInvestor at Foundation CapitalMaroof AhmedFounder at Octopus VenturesJustin SwartPartner at Bitkraft Esports VenturesVictor SantosVictor Scout at One Way VenturesSwapnil JainCEO, Observe.AI at EMERGENT VENTURESChase AdamPartner at Very Serious Ventures

+ 1,994 more

Also attended Leaders In Tech22

Nick FitzInvestor at Juniper Ventures Management, LlcJoe GreensteinPartner at Very Serious VenturesCameron PeakePartner at Restive VenturesMaria AlegreManaging Partner at Flori VenturesMaria AlegresManaging Partner at Flori VenturesDavid CarricoManaging Partner at Johnson & Johnson Innovation – JJDC

+ 16 more

Also attended New York University355

Gabriella GiglioHR & Executive Talent at General CatalystAndrea EchstenkamperVP of Marketing at HeavybitRami BranitzkyPartner at Sapphire VenturesZach WhiteInvestment Team at 8VCAnkita TiwariPrograms Manager at StartXUri LopatinInvestor at Khosla Ventures

+ 349 more

Shared employers

Also worked at Leaders In Tech9

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

+ 3 more

Also worked at Remote11

Niko BonatsosInvestment Team at General CatalystHannah SealInvestor at Index VenturesJan HammerInvestor at Index VenturesIsaiah Baril-DoreInvestor at Index VenturesKarly WentzPartner at B4 CapitalFrank LansinkSenior Partner at Inkef

+ 5 more

Also worked at 500 Global137

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 VenturesDannyInvestor at MGV.VC

+ 131 more

Also worked at CRV56

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

+ 50 more