Anthony Casalena
Background
Anthony Casalena was born in Maryland and studied computer science at the University of Maryland, College Park. Frustrated by the lack of cohesive, well-designed web publishing tools, he founded Squarespace from his dorm room in 2003.
Role at Squarespace, Inc.
Anthony Casalena is the Founder and Chief Executive Officer of Squarespace, Inc. Over two decades of continuous leadership, Casalena guided Squarespace from a solo bedroom project into a $7.2 billion global software titan generating over $1.2 billion in annual recurring revenue. Casalena's relentless focus on aesthetic craftsmanship, design typography, and disciplined capital management established Squarespace as one of the most resilient and profitable SaaS businesses in modern history. He guided the company through seven years of solo bootstrapping, institutional venture funding from Accel and General Atlantic, a 2021 NYSE direct listing, and its landmark $7.2 billion acquisition by Permira in 2024. Casalena is celebrated as one of the most disciplined tech founders of his generation, retaining significant equity ownership and operational leadership throughout Squarespace's evolution into a global design icon.