Founder & Chief Executive Officer
Anthony Casalena is the Founder and CEO of Squarespace, which he started from his dorm room in 2003. During the company’s early years, Anthony acted as the sole engineer, designer, and support representative for the entire Squarespace platform. In addition to running the company and setting overall product strategy, he remains actively involved in many departments of the company that he had previously run himself. Anthony holds a Bachelor of Science in Computer Science from the University of Maryland.@acasalena
Chief Financial Officer & Chief Operating Officer
Nicole brings to Squarespace 20 years of experience building new businesses and transforming legacy business models. Most recently, she served as Chief Financial Officer at Infor, one of the largest providers of enterprise applications in the world. Prior to Infor, Nicole spent 17 years in various operational and financial leadership positions within IBM’s Cloud Computing, Global Services, and Software organizations. She holds an MBA from The Wharton School of the University of Pennsylvania and a Bachelor’s degree from New York University.
Senior Vice President, Strategy
As the leader of Squarespace’s Strategy division, Andrew is responsible for developing the analytical frameworks that shape the company’s business. Since joining Squarespace, he has grown the division into a team that covers everything from business strategy and customer insights to analytics and data science. Prior to Squarespace, Andrew worked at the New York County District Attorney’s Office helping to shape the office’s new data-driven approach to fighting crime. Andrew graduated from Yale, where he majored in Psychology and was an editor at the Yale Daily News.
Senior Vice President, Engineering
John Colton, SVP of Engineering, oversees Squarespace’s vast engineering organization which drives the core programming for the company. Before joining Squarespace, John served in senior leadership roles at a number of organizations including database security vendor Application Security, business and service assurance vendor Micromuse, and videoconferencing vendor VisualScape. John began his engineering career at Cap Gemini America where he developed network management products for AT&T Network Systems. He received his B.S. in Computer Engineering from Lehigh University.
Vice President, Customer Operations
Rapha leads Squarespace Ireland and oversees the company’s global Customer Operations teams that support millions of Squarespace users. Prior to this role, Raphael spent eight years at Google developing and managing different operations teams in Brazil, Argentina, Poland and Ireland. A Brazil native, he has 20+ years of experience in the tech world, working in a number of marketing and strategy positions in multinational companies such as FCBi, BellSouth, and Realmedia 24/7. Raphael is a mechanical engineer by trade with an MBA in Marketing.
Vice President of Product, Consumer Products
As a Vice President of Product, Natalie leads the product managers who are responsible for Squarespace's core CMS, commerce features, marketing tools, analytics, and mobile app products. She partners closely with leadership in the Design and Engineering Teams to articulate a clear product vision, set well-defined product goals, and guide products from conception to launch. Previously, she founded TrailTalks, a non-profit educational organization based in Israel. Natalie holds a BA in Philosophy, Politics, and Education from the University of Oxford.
Chief People Officer
As Chief People Officer, Mary leads Squarespace’s People team, where she is responsible for the company’s talent and culture. She oversees human resources, people operations, talent acquisition & development, facilities & workplace services, employee experience, and diversity & inclusion. Mary has 20+ years of experience leading People functions at high-growth SaaS companies, and was most recently Chief People Officer of Fuze, a global, cloud-based unified communications platform that empowers productivity. Prior to that, she held leadership roles at tech companies including hCentive, Blackboard, CACI, SRA International, and AMS, Inc. Mary earned her MBA with a concentration in Human Resources Management from Syracuse University and received her undergraduate degree in Human Development and Family Studies from The Pennsylvania State University.
Chief Creative Officer
As the Chief Creative Officer of Squarespace, David Lee leads the company’s award-winning creative team, whose work encapsulates all brand creative, web design, and product design efforts for the company. In 2017, he was named one of the Most Creative People in Business by Fast Company. Since joining Squarespace, David has master minded five Super Bowl campaigns. Prior to Squarespace, David served as Worldwide Digital Executive Creative Director of TBWA Worldwide and as a Creative Director at Wieden+Kennedy and AKQA. He graduated from RISD with a BFA in graphic design.
Chief Marketing Officer
As the Chief Marketing Officer of Squarespace, Kinjil leads the company’s world-class marketing and PR teams. Prior to joining Squarespace in 2017, Kinjil served as CMO at Foursquare where she successfully repositioned the company’s brand to accelerate growth in both the consumer and enterprise location intelligence businesses. Kinjil spent the previous decade building technology competencies for retail giants, most notably as Vice President of Digital Marketing for Saks Fifth Avenue. She has been named to Adweek’s ranking of the top 20 Tech Savvy CMOs driving innovation and one of Adweek’s Young Influentials, along with Forbes’ inaugural CMO Next list. Kinjil holds a bachelor’s degree with Honors from the University of Texas at Austin in Management of Information Systems and Finance.
Vice President, Channels & Services
Roberta leads the newly formed Channels & Services department that focuses on developing and scaling new Squarespace customer segments and service offerings. Roberta recently rejoined Squarespace after being Vice President, Operations at Policygenius. Roberta was previously the NY based Vice President overseeing the global Customer Operations teams that support millions of Squarespace users. Prior to Squarespace, Roberta launched WSJ+, the Wall Street Journal’s first customer membership program, and served as AVP of Operations and Systems at AIG. She started her career at Bloomberg L.P., leading several global support teams and acting as the COO of the Analytics department. Roberta holds an MBA from the University of Oxford and a B.S. in Policy Analysis and Management from Cornell University.
As General Counsel of Squarespace, Courtenay oversees the company’s global legal activities and policies across all aspects of the business. Prior to Squarespace, she served as Deputy General Counsel of Gizmodo Media Group, LLC where she led the legal department and provided counsel on a number of areas including editorial content, product, advertising, litigation, and corporate transactions. Earlier in her career, Courtenay was Counsel for The Hearst Corporation, a law clerk in the Eastern District of New York, and an associate at Simpson Thacher & Bartlett LLP. She holds a J.D. from The University of Michigan Law School and a B.A. from Wellesley College.
Vice President, Acuity
As Vice President of Acuity, Gavin leads Squarespace's appointment scheduling product, focusing on support for service-based businesses. Before joining Squarespace, he helped small businesses offer and manage appointments online as the founder and CEO of Acuity Scheduling. Under his leadership, Acuity grew from an idea to a profitable business used to schedule tens of millions of appointments annually. Gavin, who joined Squarespace as part of the acquisition of Acuity, holds a B.S. in mathematics from Penn State University.
Board of Directors
Founder & CEO
Co-Founder, Former CEO & Deputy Chairman
Board Member & Former President
Chief Financial Officer