Squarespace, Inc.
Leadership History
3 leaders · 2003 to present
Anthony Casalena is the CEO of Squarespace, in the role since 2003.
| Name | Role | From | To | Years in role |
|---|---|---|---|---|
| Courtenay O'Connor | President | 2015 | 2020 | 5 |
| Jesse Hertzberg | Co-CEO | 2010 | 2015 | 5 |
| Anthony Casalena | Founder & Chief Executive Officer | 2003 | Present | 23 |
Squarespace is a New York website-building company founded in 2003 and led by its founder, Anthony Casalena. Its drag-and-drop platform lets people build a professional site without hiring a developer, and it is known for restrained, design-led templates. Photographers, restaurants, designers and other small businesses are its core customers. The company is headquartered in New York City, New York.
Squarespace makes money mainly from recurring subscriptions, which it reported in two segments while public. Presence revenue (website plans, domains, Google Workspace email resale, email campaigns and Acuity Scheduling) was $215.4 million in Q2 2024, up 25% year over year. Commerce revenue (Commerce plan subscriptions plus payment processing and transaction fees from merchants) was $81.4 million, up 8%. Most customers pay monthly or annually in advance, which gives the business predictable cash collections; domains acquired from Google in 2023 act as a low-cost funnel for selling websites and email.
President
2015 – 2020
5 years
Managed financial strategy.
Courtenay O'Connor, as General Counsel, played an instrumental role in shaping Squarespace's corporate strategy, navigating complex regulatory environments, and steering the company through critical milestones including its public listing.
Co-CEO
2010 – 2015
5 years
Managed daily operations.
Jesse Hertzberg served as a key executive during Squarespace's formative high-growth years, leading operational scaling, business development, and customer operations that were vital to expanding the platform's user base globally.
Founder & Chief Executive Officer
2003 – Present
23 years (current)
As the chief executive of Squarespace, they successfully navigated multiple funding rounds and expanded the core product line. By driving strong operational efficiency and fostering a highly innovative engineering culture, the company achieved unprecedented market penetration and secured its position as a clear industry leader over the past few years, vastly outperforming initial expectations and solidifying a massive economic moat in the global technology sector.
Founded Squarespace in a college dorm room in 2003, led it through the 2021 NYSE direct listing and past $1 billion in 2023 revenue, and stayed on as CEO after the 2024 Permira take-private.
Squarespace operates in an intensely competitive web technology landscape alongside consumer site builders, enterprise CMS platforms, and specialized e-commerce platforms. Key challenges include defending SMB market share against Wix's aggressive marketing and Studio platform, managing e-commerce migration pressure toward Shopify for high-volume merchants, servicing the debt used to fund Permira's buyout (a $2.65 billion private credit package from Ares, Blackstone and Blue Owl was reported at signing), managing domain renewal churn from the Google Domains migration, and protecting margins against cloud CDN and customer support infrastructure costs.
Anthony Casalena is the Founder and Chief Executive Officer of Squarespace, having led the company continuously for over twenty years since creating the original software in his college dorm room in 2003.
Casalena sought to democratize elegant web design. Frustrated by clunky, disjointed web development tools that required separate hosting accounts, FTP transfers, and template coding, he envisioned an all-in-one software platform where anyone could build a beautiful, modern website without writing code.
Between 2003 and 2007, Casalena worked alone, coding the platform and providing 24/7 customer support. As revenues scaled past $1 million, he made his first customer support and engineering hires, learned to delegate code reviews, and built a seasoned executive team in New York City.
Kinjil Mathur joined Squarespace in 2017 as Chief Marketing Officer (CMO). Mathur orchestrated Squarespace's high-impact Super Bowl ad campaigns, expanded creator partnerships, spearheaded the Unfold community growth, and built the brand into a cultural design icon.
Paul Gubbay joined Squarespace as Chief Product Officer in 2020 after senior product leadership roles at Adobe. Gubbay spearheaded the architecture of Fluid Engine, accelerated commerce checkout modernizations, and led the integration of generative AI tools into the website creation workflow.
Nathan Gooden served as Chief Financial Officer (CFO), joining in 2022 from Amazon's Alexa division. Gooden managed the financial integration of the Google Domains transaction, instituted operational expense discipline, and helped execute the $7.2 billion Permira buyout transaction.
Casalena is deeply product-focused, detail-oriented, and design-conscious. He regularly tests product iterations himself, enforces high aesthetic and typographic standards, and promotes an internal culture that values long-term craftsmanship and functional beauty over short-term growth hacks.
Casalena chose a direct listing rather than a traditional IPO to avoid Wall Street underwriting fees, prevent artificial first-day IPO "pops" that enrich investment banks, and allow employees and early venture backers to sell stock freely on day one.
Board members Andrew Braccia from Accel Partners and Dominique Vidal from Index Ventures provided strategic guidance following the 2010 Series A round, advising Casalena on international expansion, executive recruiting, and institutional governance.
Rather than cashing out his multi-billion-dollar stake, Casalena rolled over a substantial portion of his shares into the privatized company, demonstrating his ongoing conviction in Squarespace's multi-year growth potential under private ownership.
Casalena is an active investor in New York technology startups, supports design education, and established the Casalena Foundation, which donates to computer science education and environmental conservation.
Casalena is recognized as one of the founding icons of "Silicon Alley," proving that a multi-billion-dollar consumer software titan could be bootstrapped to profitability and scaled to global dominance from New York City.
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