Cherry is Shutting Down + Our Story

Gillian O'Brien
2 min readMay 4, 2020


After 18 months of helping workplaces become more personalized, we’ve made the difficult decision to shut Cherry down. While Cherry helped spearhead a new way to provide modern benefits to employees, a confluence of factors have hindered our ability to raise funding. We’ve decided to share our journey to help other founders, provide a case study to learn from and to memorialize what we accomplished.



  1. We’ve been operating Cherry for a year and a half as a team of 2 full-time people (1 engineer). Despite resource constraints, we were able to accomplish a lot that we’re proud of including: launching 2 versions of our product and acquiring 1,000+ users across 39 customers, many of whom genuinely loved Cherry with a nearly 90% engagement rate.
  2. Users & revenue grew 57% MoM for 6 months — although in the end it was not enough to be profitable (current MRR: ~$5,000).


  1. Operated too long with just two co-founders, in a too crowded market.
  2. Seed raise co-incided with COVID, and investors weren’t willing to take the risk given the 1) “vitamin” nature of perks, 2) competitive landscape, 3) COVID and their new risk tolerance.

We’ve broken down our story into 5 short articles:

💡 How It Started

🌁 Silicon Valley n00bs

💰 How Not To Fundraise

📈 A New Product & An Upward Graph

🦠 Fundraising During COVID

Though we’re disappointed to be shutting down, we truly feel that running Cherry was a net win and we could not be more grateful to have had the opportunity to serve our customers and grow alongside them. This experience has given us invaluable tools and skills that we’re excited to bring to our next roles and future startups.

We’re looking for our next opportunity if you want to connect you can reach us on LinkedIn:





Gillian O'Brien

Accelerator Partnerships @ + Venture Partner @ OCVC | YC alum | former Chief of Staff | NYU grad |