Leena.ai: Early Advisor & Angel Investor

Dipankar Sarkar
Dipankar Sarkar · · 1 min read

About Leena.ai

Leena.ai is an enterprise HR AI company. I wrote the first angel check in 2017 when the company was still called ChaterOn, and I worked closely with the founders on the pivot to HR AI, the YC W18 application, and the early go-to-market.

Outcomes

  • 2017: First angel check (ChaterOn)
  • 2018: Pivoted to enterprise HR AI, joined Y Combinator (W18)
  • 2018: Series A $8M
  • 2019: Series B $30M
  • 2018+ — ongoing: “From Chatbot to Enterprise AI” case study

My Role

  • Early advisor on the HR vertical pivot, YC application, and Oracle engagement
  • Angel investor (first check)
  • Ongoing board observer until Series A

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