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Gillian OBrien

Founder

Founder at Cherry

United States

FoundedCherry · YC

Find your path to Gillian

1,021 people in our graph share verified history with Gillian — schools, employers, funds. One of them is your warm intro.

Niko BonatsosunlockedGillian: together at Remote (2023–2026)
×2Gillian: together at Remote
×2Gillian: together at New York University
×6Gillian: together at 500 Global

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) — any YC alum in your network can reach them through the YC community.

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

Cherry's investors · 2

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

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

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.

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

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