How Super Bowl Advertising Turned Squarespace into a Success
In the world of digital brands, few have leveraged traditional advertising as powerfully as Squarespace. While many startups focus solely on digital-first strategies, Squarespace took a bold leap in 2014 - investing a significant portion of its revenue into a Super Bowl commercial. It was a high-stakes move for a company built on sleek web design, but the gamble paid off spectacularly.
What started as a single, ambitious ad buy quickly became a cornerstone of the brand’s identity, cementing Squarespace as a household name. Over the years, the company’s Super Bowl campaigns have featured A-list celebrities, visionary directors, and storytelling that seamlessly blends creativity with commerce. But how exactly did this strategy transform Squarespace from a niche service into a mainstream success?
Let’s explore the game-changing role the Super Bowl played in Squarespace’s rise.
In 2007, Squarespace's annual revenue was $1 million. By 2015 the company had achieved $100 million in revenue. In 2017, the company was valued at $1.7 billion and in 2021 when the company went public, its valuation at its Initial Public Offering was $6.8 billion.
Squarespace has been skilled at using performance media to boost brand awareness and attract new users. But it was not until 2014 that Squarespace took a bold new step, diving into uncharted waters by airing its first Super Bowl commercial.
The big game was Super Bowl XLVIII, featuring a matchup between the Seattle Seahawks and the Denver Broncos, led by veteran quarterback Peyton Manning. The halftime show featured performances by Bruno Mars and the Red Hot Chili Peppers, drawing over 100 million viewers.
The first time Squarespace appeared on the Super Bowl, its ad expenditure was more than 10% of the company’s revenue. The company partnered with Quigley-Simpson, an independent, performance-based advertising agency specializing in brand response. Quigley-Simpson negotiated and maximized the value of Squarespace’s advertising inventory in and around the Super Bowl as well as in other sports programming on the Fox Network which carried the big game that year.
Squarespace's inaugural Super Bowl venture proved to be a resounding success, prompting the company to not only deem a future Super Bowl investment essential, but also to begin adopting a progressively bolder approach each subsequent year. In 2015, NBC carried the Super Bowl and Squarespace's results continued to be successful, using the same media buying approach as the year before. This included enlisting high-profile talent and crafting integrated, elaborate storylines with the potential to resonate well beyond the event itself.
A Look Back at the Milestones and Previous Super Bowl Appearances
2014
Squarespace estimated annual revenue - ~$100M
In 2014, Squarespace introduced a 30-second advertisement named "A Better Web Awaits." This commercial unfolds in an alternate reality, vividly embodying both the positive and negative aspects that people associate with the Internet. The protagonist of the story encounters a diverse array of characters, each representing various Internet archetypes and memes familiar to viewers. The purpose of the ad is to illustrate Squarespace's stance against certain aspects of the web while emphasizing the company's commitment to fostering a superior web experience.
2015
Squarespace estimated annual revenue - ~$200M
In 2015, Squarespace enlisted actor Jeff Bridges for a commercial part of Squarespace's "Build It Beautiful" campaign. Jeff Bridges appeared in a dreamlike sequence where he sat in a recording studio and used Squarespace to create a website for his sleeping tapes. The TV spot effectively conveyed the message that Squarespace could help users build visually appealing and functional websites for a variety of purposes.
Squarespace's inaugural appearances in the Super Bowl had a remarkable impact, fostering heightened awareness and setting new records for website visits immediately after the commercials aired.
This bold foray into a realm where only a handful of performance brands venture, established a trajectory that empowered Squarespace to take even bolder strides in the years that followed.
2016
Squarespace estimated annual revenue - ~$250M
In 2016, Squarespace released a commercial titled "Real Talk with Key and Peele." The commercial featured comedians Keegan-Michael Key and Jordan Peele in a humorous sketch that portrayed the absurdity of traditional sports commentary. In the spot, the comedians provided commentary on a fictional sport called "Flopping," highlighting the comedic aspects of over-the-top reactions in sports. The ad effectively conveyed Squarespace's message about standing out and being different in the online world.
2017
Squarespace estimated annual revenue - ~$300M
Squarespace’s 2017 Super Bowl spot featured actor John Malkovich and was titled "Calling JohnMalkovich.com." In the commercial, Malkovich discovers that someone has bought the domain name johnmalkovich.com on Squarespace, leading to a humorous and surreal interaction. Many viewers and critics praised the creative and unique concept, as well as Malkovich's performance. The commercial went on to win an Emmy Award for Outstanding Commercial. The commercial effectively showcased Squarespace's ability to help individuals create and manage their websites.
2018
Squarespace estimated annual revenue - ~$390M
In 2018, Squarespace returned to the Super Bowl with a commercial titled "Make It Happen”, featuring actor Keanu Reeves. The ad showcased Keanu Reeves riding a motorcycle through different scenes, emphasizing the idea of making your dreams a reality and using Squarespace to create a website for your business or personal project. The reception to Squarespace's 2018 ad was mixed, although overall, it generated discussions about the use of celebrities and storytelling in Super Bowl commercials.
2020
Squarespace estimated annual revenue - ~$620M
Squarespace took a break from the Super Bowl in 2019 but returned in 2020 with a commercial that featured actress Winona Ryder and was titled "Winona in Winona." The ad showcased Winona Ryder creating a website for her hometown of Winona, Minnesota. It highlighted Squarespace as a tool for small businesses and local initiatives. Viewers appreciated the nostalgic and heartwarming approach of featuring Winona Ryder and her connection to the small town of her birth.
2021
Squarespace estimated annual revenue - ~$784M
Listed on the NYSE This Year
In 2021, Squarespace tapped singer-songwriter and CEO Dolly Parton for Super Bowl LV to rework her country classic for the modern day. The commercial begins in a mundane setting of an office space where employees struggle to get through the workday, but when the clock strikes 5, these everyday employees transform into passionate entrepreneurs, with Squarespace enabling them to take on the world. Dolly Parton’s classic song, 9-5 is reworked as “5 to 9”, to celebrate the entrepreneurial spirit. A call to action at the end of the spot encourages viewers to visit Squarespace.com to listen to the entire reworked song.
2022
Squarespace estimated annual revenue - ~$867M
During Super Bowl LVI, actress Zendaya played the role of Sally, an entrepreneur selling “seashells by the seashore”. After failing to acquire customers, Sally uses Squarespace to create an online store, which turns the business into a huge success as Sally diversifies and expands her seashell business. The commercial is narrated by Andre 3000 and retains hints of the tongue-twisting storyline from the original nursery rhyme.
2023
Squarespace estimated annual revenue - ~$1B
In Super Bowl LVII, Squarespace adopted a darker comedic approach in its commercial, titled "The Singularity," showcasing the talent of actor Adam Driver. The ad opens with the enigmatic idea that Squarespace is a website that creates other websites. Adam Driver contemplates this curious notion in isolation within a desert landscape, where his presence begins to multiply. As his duplicates increase, reality warps around him, leading to a singularity event. This innovative concept seamlessly extended to a dedicated landing page, urging users to explore a limited-edition singularity template or to "build a website with Adam Driver.“, which featured an interactive website-building program centered around the concept of the TV commercial.
2024
Squarespace estimated annual revenue - ~$1.2B
Last year, Squarespace marked its 10th Super Bowl appearance with a bold, cinematic ad directed by none other than Martin Scorsese. The spot took a clever, satirical jab at modern digital obsession, portraying a world so engrossed in screens that no one notices an alien invasion unfolding around them. In a twist of irony, the extraterrestrials themselves turn to Squarespace to break through the digital noise—crafting a message that finally captures humanity’s attention. It was a smart, self-aware take on the very challenge brands face today: cutting through the clutter to truly connect.
Following its $7.2 billion acquisition by Permira, Squarespace has cemented its position as a leading Software as a Service (SaaS) powerhouse. Of course, several factors beyond its notable appearances in the Super Bowl have contributed to Squarespace’s success. But it is primarily the unwavering, bold attitude—taking on challenges like advertising on the Super Bowl—combined with the courage to follow through on its marketing efforts that have fueled the company's remarkable growth. It is a reminder that thinking outside the box often means taking calculated risks. Not by being reckless, but by strategically leveraging marketplace insights, brands can propel themselves to new heights.
For marketers, envisioning long-term growth requires outsize steps to achieve it. In today's fast-paced landscape, short-term goals often dominate decision-making, yet Squarespace’s continued investment in high-impact brand storytelling proves the enduring value of insight-driven brand building with performance as a key underlying variable.
2025
As we tuned in to Super Bowl LIX on February 9th, 2025, we witnessed Squarespace’s 11th big-game appearance—this time with a playful, cinematic spot featuring Barry Keoghan and an unlikely protagonist: a donkey named Don Mosley.
The ad, set against the scenic Irish countryside, leaned into humor and storytelling to reinforce Squarespace’s core message: anyone can build an impactful online presence, no matter where they start. The brand’s ability to blend creativity with product utility has been a hallmark of its Super Bowl strategy, proving once again that bold, well-executed campaigns can drive both awareness and business growth.
Which new brands taking their first bold steps on the Super Bowl stage in 2025 will emerge as market leaders in the decade ahead?
The Super Bowl, beyond its spectacle, remains a stage for audacity and potential industry game-changers. After all, it was on this very platform that Apple launched the Macintosh in 1984—more than forty years ago—ushering in a new era of technology. And that's a whole other remarkable case study.
© 2025 The Continuum
February 1, 2024 | Updated February 10, 2025
