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Founder & CEO of Squarespace

Anthony Casalena is the Founder and CEO of Squarespace, the design-driven platform helping millions of entrepreneurs worldwide build brands and businesses online. Anthony created and launched Squarespace from his dorm room at the University of Maryland in 2003, and acted as its sole operator and developer for years – covering roles ranging from engineering and marketing to customer support. Under Anthony’s continued leadership, Squarespace has grown from a single person, bootstrapped startup to a global, profitable, publicly listed company (NYSE: SQSP) with over $1B in annual revenue and 1,800 employees globally. Anthony was named to Fortune’s 40 under 40. He is an avid public speaker, appearing on CNBC, Bloomberg, How I Built This on NPR, Decoder on The Verge, WSJ Tech Live Conference, and the 20VC podcast, among many others. Residing in Manhattan, Anthony holds a B.S. 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 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.

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 People Officer

As Chief People Officer, Angela Crossman leads the company’s People organization. Angela is a people-first, hands-on leader with a background that spans from employee experience to compensation, organizational performance, talent development and more. Angela brings extensive experience and leadership in corporate human resources to her role. Prior to joining, she served as the Chief People Officer at Dragos, Brex and Noom. She also held the position of Executive Vice President of Talent, Operations, and Global People Analytics at Bain & Company. Angela’s background includes a business and consulting focus from her earlier time as Vice President of Strategy and Business Operations at Yahoo and other roles. She holds an MBA in Strategic Management from Wharton.

Chief Creative Officer

David is the Chief Creative Officer of Squarespace, leading their award-winning team, whose work encapsulates all brand strategy, creative, design and production for the company. David has been honored as the Brand CCO of The Year by Ad Age in addition to his team becoming Ad Age In-House Agency of the Year. During his time, Squarespace has been honored as the Brand of the Year by the Art Directors Club, and the number one globally awarded in-house agency of the year at the One Club for Creativity. David has won an Emmy Award, been included in the Adweek Creative 100 List and named as one of the Most Creative People in Business by Fast Company. He has also been recognized by the Gold House A100 list, honoring Asian Pacific leaders who made the greatest impact on culture and society. Prior to Squarespace, David served as Worldwide Executive Creative Director of TBWA and as a Creative Director at Wieden+Kennedy and AKQA. David graduated from the Rhode Island School of Design and currently serves as their Co-Chair, Officer of the Board.

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.

Chief Customer Officer

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.

SVP, Head of Domains & Applications

As SVP of Domains & Applications, Kevin Doerr leads Squarespace’s General Manager (GM) organization, overseeing key business lines including Domains, Acuity Scheduling, and Social Products (Unfold, Bio Sites). He is responsible for driving growth, scaling these offerings, and integrating them across the Squarespace ecosystem. Kevin joined Squarespace in 2024 to lead the Domains business, bringing over 30 years of experience in domains, DNS, consumer applications, fintech, and payments. He has served as Chief Product Officer at DailyPay, Inc. and Marqeta and has held leadership roles in both the domains and security spaces. He also co-founded Archimedes Labs. Kevin’s career began in software development before transitioning into leading multi-disciplinary teams across technology and business functions.

SVP, Growth

As Senior Vice President of Growth, Josh Groth leads the strategies behind Squarespace’s media investment, CRM, and international expansion. Josh brings 18 years of experience scaling technology companies across both B2B and B2C. At Squarespace, his focus is on helping entrepreneurs worldwide turn their ideas into thriving businesses. Prior to joining the company, he served as VP, Growth at Hims and SVP, Global Performance Marketing at Square, where he established a global center of excellence for acquisition and creative production. His earlier career includes growth roles at Meta and Grove Collaborative. Josh is a firm believer that the most impactful growth happens at the intersection of rigorous data and genuine creative curiosity. He received his B.S. in Business Administration from the University of Oregon.