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Richie Chaikof

Richie Chaikof

New York

Focus Area


Richie focuses on investments in application software and SaaS companies. He is based in New York City and works across all aspects of the investment process.

Prior to joining Bain Capital Ventures, Richie worked in investment banking across three different geographies, including New York, Toronto and Tel Aviv.  Most recently, he worked in the Technology Investment Banking Group at Citi in New York, and spent time with Barclays Capital in Tel Aviv. Richie has been a part of a variety of M&A and capital markets transactions in the software, internet and IT services spaces.

Richie’s interest in creating global partnerships led to his founding of The Aleph Group, an apolitical and non-religious pro-bono consulting organization that connects Canadian business students with the Israeli startup ecosystem.

Richie was born and raised in Toronto, Canada. He enjoys water and downhill skiing, all things James Taylor, and watching the Toronto Blue Jays.


He graduated with distinction from the Ivey Business School at Western University, where he served in student government and played on the varsity baseball team.