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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.

Chief Financial Officer & Treasurer

As Chief Financial Officer and Treasurer, Nathan Gooden oversees finance, treasury, and corporate development functions at Squarespace. Nathan brings more than 25 years of financial experience. He joins Squarespace from Amazon where he acted as the Chief Financial Officer of Amazon Alexa WorldWide for over five years. Prior to Amazon, Nathan served as Chief Financial Officer across several fields, including payments, social commerce, and consumer electronics. Gooden began his career at PricewaterhouseCoopers, where he spent five years as a lead auditor. He holds a Bachelor of Science degree in Accounting from Oral Roberts University.

Chief People Officer

As the Chief People Officer at Squarespace, Jarlath Doherty oversees the People and Internal Communications organization, ensuring that our people remain at the heart of our success. Jarlath has over 20 years of experience in HR with proven expertise in HR strategy, transformation, and process optimization. He is responsible for all aspects of the employee lifecycle including talent acquisition, management, and development; compensation and benefits; people operations and analytics; employee engagement, D&I and social impact. Before joining Squarespace, Jarlath spent over 7 years as Chief People Officer at Collibra, where he oversaw the People, Workplace and IT teams for a global team of 1,250 during a period of rapid expansion, while proving his ability to optimize HR services and drive operational efficiency. Earlier in his career, he excelled in People leadership roles across various tech companies including LinkedIn and Yahoo!. Jarlath earned his Masters of Science in Computing and Information Systems from Ulster University in the UK.

Chief Product Officer

As the Chief Product Officer of Squarespace, Paul oversees the product organization, which encompasses Product Management and Product Design. Prior to joining Squarespace, Paul spent 15 years at Adobe as VP of Design and Web, responsible for a wide span of Adobe’s Creative Cloud products including Illustrator, Indesign, XD and Spark. He joined Adobe through its acquisition of Macromedia in 2005, where he ran Product Development for Dreamweaver and Flash Professional. He developed his passion for the Web as a Co-Founder and CEO of CyberSage, a flash application software company that was acquired by Macromedia in 2003.

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.

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 Technology Officer

John Colton, Chief Technology Officer, 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.

General Counsel

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.

Senior Vice President, Customer Operations

Rapha leads the company’s Customer Operations department, overseeing global teams that support millions of Squarespace users. Initially based in Dublin, Ireland, he was responsible for setting up Squarespace’s European headquarters and helped accelerate our international expansion. Before joining Squarespace, Rapha spent eight years at Google developing and managing different operations teams in Brazil, Argentina, Poland and Ireland. A Brazil native, he has 25+ 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. Rapha is a mechanical engineer by trade with an MBA in Marketing.

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.

Senior Vice President, Head of Tock

As the Head of Tock, Matt oversees the commercial success and growth of our Tock business which includes a reservation system, table management, carryout operations, and events for operators across 33 countries. Matt came to Squarespace with nearly two decades of experience building teams and operating companies of all sizes and has a strong background in hospitality tech and the startup world. Most recently, Matt served as President & Chief Operating Officer of Olo, the leading provider of SaaS solutions to the chain restaurant industry, serving almost 90,000 locations across North America. Matt spent nearly nine years at Olo, taking the company from 10 people and one product to a public company with over 700 people, six core products, and nearly $200mm in revenue. Prior to Olo, Matt was on the founding team of LendingTree and was also the founder of Rely Software. He holds an MBA from Georgetown University and a B.A. in Political Science from The University of Michigan.

Senior Vice President, Commercial

As the Head of Commercial, Dan is responsible for commercialization across all of our brands, including pricing, monetization, packaging, bundling, checkout, and payments as well as fostering the success of Acuity Scheduling. Prior to Squarespace, Dan was Senior Vice President of Strategic Development at MINDBODY, the popular online scheduling and business management software for the wellness industry, where he spent 5 years running Payments & Business Development. Before that, he held a variety of leadership roles at Booker Software, where he spent nearly 11 years of his career prior to Booker’s acquisition by MINDBODY. He also has over a decade of experience dealing with payment platforms and payment platform integrations – which were instrumental to the success of his prior companies.