Keith Rabois Leaves Top Operating Role At Square

Long-time investor and Valley executive Keith Rabois is leaving his chief operating officer position at payment company Square, according to a surprise announcement by the company tonight. Chief financial officer Sarah Friar will be acting COO while it looks for a replacement.

Rabois joined Square in August 2010 and developed most non-product parts of the company, including marketing, communications, business development, distribution, human resources and risk management, according to his CrunchBase bio.

There’s more than one way to decipher the reason based on the statements from Rabois and founder Jack Dorsey, below:


Today I accepted Keith’s resignation from Square. When he joined, we had fewer than 30 employees and under 1000 active merchants. Today, over 3 million individuals and businesses are able to accept credit cards with Square, processing over $10 billion annually. We couldn’t have done it without him and we wish him well in his next opportunity.


It is amazing what Square has accomplished since August of 2010. When I joined, there were 17 engineers all reporting flatly to Jack. The local coffee shop served as our interview room. Leading our amazing crew has been the most rewarding professional journey of my life. I am forever grateful to Jack, for his confidence in me and to each and every member of the team for allowing me to learn from them.

But every day matters. And it is better at this point for me to be doing something different every day.

As a result, I’ve decided to resign from Square. I am very excited about what lies ahead for the company. Square could not be better poised for greatness.

I will have more to share about my next opportunity soon.

They both mention a next opportunity, which suggests that part was planned out. Having Friar come in as an acting COO suggests that part was not — although Friar is widely respected, and her move into the position doesn’t necessarily mean his departure was a huge surprise internally.

An often outspoken figure in Silicon Valley, Rabois also serves on the boards of Yelp and Xoom, is an occasional angel investor, and was an early executive at PayPal, LinkedIn and Slide. He didn’t comment when I reached him tonight, except to say that he’ll share more soon. Square, meanwhile, is having an all-hands meeting tomorrow to discuss his departure, according to sources.