Startup Stories: Lessons Learned From Winding Down Cherry

When Gillian O'Brien co-founded Cherry, she was ready to disrupt the HR space with a modern employee perks platform. But, after initial success—joining Y Combinator, raising a $700k+ angel round, and acquiring 40+ paying customers, they made the difficult decision to wind down Cherry.

Watch a recorded conversation between of Gillian and Pilot co-founder and CEO Waseem Daher. They discuss Cherry’s journey and the invaluable lessons learned along the way, including:

  • Building a product in a crowded market
  • Leading your fundraising process
  • Sunsetting your business and deciding what’s next
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Gillian O’Brien

Gillian was the founder of Cherry, a flexible benefits marketplace that let employees choose their perks. With her co-founder and sister, Emily, she took the company through YC in 2019. Cherry shut down after 1.5 years, and Gillian now works as the Chief of Staff at Dover.

Waseem Daher

Waseem is the co-founder and CEO of Pilot. He is a three-time entrepreneur with two successful exits working with the same founding team: his first company, Ksplice, was acquired by Oracle in 2011 and his second, Zulip, was acquired by Dropbox in 2014.

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