Season 1, Episode 5 with Matt Tucker was originally released on March 15, 2023.


Matt Tucker, Senior Vice President of Squarespace and the Head of Tock, has ridden the technology wave. He’s had a lot of success riding in the Tube, but he’s also been in the Impact Zone more than anyone would care to experience. Matt shares stories of choosing between his career and being more available for his family, becoming experienced at conducting employee RIFs, and wondering how his transportation business would survive immediately following the impacts of September 11. It should come to no surprise that even someone as successful as Matt has experiences of F’ing Up.

About Matt Tucker

Matthew Tucker is a Senior Vice President of Squarespace and the Head of Tock, a leading provider of online reservations, table management, takeout, and events solutions to the hospitality industry. 

Prior to Squarespace, Matt was the President and Chief Operating Officer of Olo, a SaaS provider to the restaurant industry. During his almost nine years at Olo, he helped grow the company from 10 employees and approximately $2mm in revenue to a 700 person company doing nearly $200mm in revenue. In March 2021, Matt helped lead Olo's successful public offering on the New York Stock Exchange. 

Immediately prior to Olo, Matt was the Chief Operating Officer of Prove.com, the leading provider of identity tokenization and passive cryptographic authentication solutions. Prior to that, Matt was the Founder and CEO of Rely Software and on the founding team of LendingTree. 

He has a MBA from Georgetown University and a BA from the University of Michigan. Matt is on the Board of 7shifts and Vita Mojo.

The views, thoughts, and opinions expressed are the speakers’ own and do not represent the

views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.