At Contentsquare, Growth Takes Many Forms

Three of the company’s leaders describe the organization’s plans to increase its headcount, refine its culture and position itself as a leader in its field.

Written by Olivia McClure
Published on Dec. 08, 2021
At Contentsquare, Growth Takes Many Forms
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For Contentsquare, a fresh $500 million in funding and the recent acquisition of analytics competitor Hotjar doesn’t just herald the beginning of a massive hiring phase. In fact, the user experience analytics platform provider is scaling in every sense.

According to Chief Marketing Officer Niki Hall, Contentsquare’s expanding headcount is really just a part of a larger move to bolster the company’s most valuable resource: its people. As the organization focuses on building a strong team, the company is eager to hire those who align with its overarching ambitions while maintaining its existing culture. 

“We invest in our team members in a number of different ways: creating opportunities for building skills, encouraging a sense of ownership and offering ample educational resources,” Hall said. “It’s important that we hire great people who want to thrive and understand their own value and that of the business and their colleagues.” 

As Contentsquare prepares to enter a new phase in its growth journey, the company is taking a closer look at various aspects of its operations, including its commitment to diversity, equity and inclusion. That’s where Global VP and Head of DEI Orly Lynn comes in. 

Since joining the organization earlier this year, Lynn said she has been busy crafting a strategy to create a more inclusive culture for both current employees and future ones. In her mind, this will be an ongoing process rather than a definitive phase in the company’s history. 

“At Contentsquare, DEI isn’t a program with a beginning and end,” Lynn said. “It’s a business imperative, and we’re not going to see that effort end anytime soon.”

For Hall, Contentsquare’s continuous transformation foreshadows an exciting future for the organization and underscores its dedication to improving the digital space. “We have grown fast and evolved significantly, but the one thing that hasn’t changed is our commitment to putting people at the heart of every digital experience,” Hall said. “We’re excited to help raise industry standards and build a world where experiences are accessible, inclusive, respectful and high quality.”

Below, Hall, Lynn and Chief Revenue Officer Chip Winslow weigh in on Contentsquare’s growth plans, as well as the company’s recent acquisition, evolving culture and market potential. 


Contentsquare teammates working together at desks company office


What teams will be seeing the most growth, and what role do these teams play in driving innovation? 

Hall: We sometimes say we have 300 people on our research and development team yet 1,000 people working on innovation. In that sense, our R&D and product teams are truly at the heart of transformation. We have plans to accelerate product innovation and expand our reach into new and existing markets, and both our product and sales teams are key to this strategy.

Winslow: As we invest in product and marketing, sales acceleration will be driven by our continued focus on acquiring new customers and expanding our footprint in our existing customer base. We will have two separate revenue-generating organizations, which will enable focus at the individual team level. 

Additionally, we will be increasing the number of leaders by twofold and sellers by sixfold. This will allow us to better cover the key segments of our total available market. Having the ability to obtain broader and deeper coverage is the key component to our next round of rapid growth. Lastly, to better help support these teams, we will expand our build-out industry solution capabilities, as well our IP and domain expertise, by leveraging our successful, diverse customer base and hiring subject matter experts in these areas.


How is the company preparing to add more than 700 new hires over the next year?

Hall: We’re creating scalable global processes and systems, which has entailed centralizing and scaling our talent acquisition org and introducing a new operating model. Additionally, we’re mobilizing our entire employee base to support shared hiring objectives. We want to ensure that there is shared ownership within the business through an internal and external referral program, launch of sourcing sprints, and strong collaboration across teams and departments. We are also building our brand while creating buzz and excitement to work for Contentsquare. Lastly, we are iterating and improving as we grow to ensure we are always one step ahead. While we’re in an important growth phase for the company, we’re also very deliberate about building a strong team that will last.


contentsquare team roof
Contentsquare company office lounge with view of nyc skyline


What is the importance of the company’s recent acquisition of Hotjar, and how do you plan to integrate the two companies?

Lynn: From an inclusion perspective, we’re going to look at how both the Hotjar and Contentsquare worlds intersect. Then, we’ll consider how we can respectfully and honorably bring those two cultures together in order to create one, which will take time. We want to design a new message that evokes the idea that we are one organization with a goal to create an inclusive workforce.



While the past two years have accelerated the pace of digital transformation, consumers still expect every brand, regardless of its size, to deliver seamless, intuitive and meaningful experiences. According to Hall, this puts Contentsquare in an exciting position to ultimately level the playing field by granting all businesses access to crucial customer insights. “Digital customer experience is every business’ business, and as consumers, we are more connected than ever before,” she said. 


Hall: Our acquisition of Hotjar allows us to expand the scope of our mission and reach. In addition to continually serving enterprise customers, we have the ability to support small and medium-sized businesses as they develop their own strategies around digital transformation and scale their operations for the digital era.


How will an inclusive culture create greater opportunities for both new hires and established employees?

Lynn: Organizations often don’t recognize that diverse people want to be part of an organization that has already carved out a space for them. People want to feel like they are a part of something that goes beyond their daily role, and they want to see their input and voice making a difference. If we don’t create a place of inclusion, we’re not going to feel that sense of belonging. We’re not going to see diverse people wanting to be a part of this organization unless we create this environment first. 



As Contentsquare continues to develop its approach to DEI, Lynn said the company offers employees plenty of ways to pitch in on that effort. For instance, the organization hosts live, bimonthly conversations with guest speakers, which enable employees to engage with each other over diversity-related topics. In addition to having access to various employee resource groups, such as ones dedicated to women in tech, differently-abled individuals and those who belong to the LGBTQ+ community, Lynn said team members can visit her privately during DEI office hours, during which time they can discuss uncomfortable issues openly and safely. 


This is the first year the company is working toward this goal internally, which is why awareness, education, engagement and data are going to be the biggest tools we use to design an intentional strategy that creates an inclusive workplace. Once we accomplish this, people will feel like they belong, and then we’ll see people of every diverse dimension bringing their best selves to the organization, where they’ll feel like they belong, they’re needed and their expertise matters. That’s my version of utopia. As a woman of color, that’s what I want to see happen and continue seeing happen for people who look like me, my family and my son. I want Contentsquare to be a space where everyone is wanted, respected, celebrated and feels as though they can bring their unique selves to the workplace.


Contentsquare company office bar


How do you balance the need to solidify the company as a market category leader and positioning it as an employer of choice? 

Hall: Contentsquare has experienced a dizzying pace of growth over the past few years, and as we’ve expanded our reach and helped define our market category, we’ve matured as an organization. We have significant aspirations regarding how we can help shape the future of the digital landscape and make a positive impact on both businesses and consumers. 

From an innovation standpoint, our ambitions are vast. Earlier this year, we acquired a deep learning company and launched the industry’s first cookie-less analytics solution. Aside from these two initiatives, we continually encourage innovation on all fronts, ranging from our internal hackathons to our incubator and accelerator program, Atomic Labs.

Simultaneously, we are building a unique company with an enviable work environment, which is its own separate adventure. We offer a corporate culture that values ideas. People want to work for companies that are ambitious and unafraid to commit to major goals, such as our work surrounding improving digital accessibility. In addition to helping brands make their digital content accessible to everyone, we’ve established the Contentsquare Foundation to raise awareness around this critical topic. 


We have significant aspirations regarding how we can help shape the future of the digital landscape and make a positive impact on both businesses and consumers.” 


As businesses acclimate to the digital landscape, what role will Contentsquare play in helping organizations thrive in the future? 

Hall: Contentsquare is already working with businesses committed to creating better experiences for their customers by understanding their goals, expectations, needs and values. Our role is to help these businesses understand their customers, which includes translating clicks, hovers and swipes into actual insights about consumers’ needs. We’re dedicated to helping brands achieve true customer-centricity and build digital trust while making sure no one is left out of their experiences and opportunities for connection. 



Images courtesy of Contentsquare. Responses have been edited for length and clarity.

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