Jonathan Cherki had a serviceable future waiting for him in Marseille. It involved beans. His grandfather had founded an import-export business in dry legumes; his father and brother worked in it. The family enterprise offered a product, a history and a place for the next generation. Then a business school project introduced a complication: Cherki became interested in the customers who disappeared between an advertisement and a purchase.
It is an oddly suitable beginning for a company concerned with human behavior. The expected route was visible. The route he took required explanation. At ESSEC Business School, where he studied before founding Contentsquare in Paris in 2012, an enthusiasm for mathematics and statistics met a problem with an everyday face. People arrived on websites. Many left. A business could count the departure without understanding much about it.
The respectable future involved beans
Cherki’s early interest was advertising efficiency. The internet had plenty of banners and plenty of ways to measure whether anyone clicked them. But a fine advertisement could deliver a visitor to a poor website. The marketing department might have done its job; the customer might still have a miserable time finding the thing they wanted. The space between arrival and checkout became the subject of his working life.
He has described his student assignment becoming a life project. That description has the advantage of being literal. Contentsquare is the company around which he has built his career, rather than a stop after a succession of employers. His business education continued inside the business. Each change in scale brought a new set of questions, and very few of them could be settled by the original assignment.
The family background matters without needing an invented rebellion. Cherki has spoken warmly about his family’s encouragement to pursue his own ambitions. The bean business supplied an entrepreneurial environment; his choice changed the merchandise. In one version of his future, goods moved between markets. In the version he chose, software helped explain what happened when customers moved between pages.
His premise is easy to grasp if you have ever abandoned a basket online. A website owner sees the shop from behind the counter. A visitor sees whatever the page happens to offer: a button, a form, a price, a delay. Cherki became interested in the distance between the experience a company intended and the experience someone actually had.
A smaller menu, a larger map
There was an early lesson in subtraction. Cherki has recalled that Contentsquare initially had seven products, then cut six to concentrate on user experience. The company also removed much of the remaining product’s scope. That is a less decorative founder story than a launch party, but a more revealing one. Developing something and deciding it deserves to survive are separate jobs.
By 2017, the map had changed. Cherki moved to New York with his family to establish the North American business. An international strategy acquired the practical dimensions of a household move. A founder can announce a market from Paris; living there means meeting it on its own terms, including the parts that fail to fit neatly into a presentation.
He later explained that physical proximity helped him understand the American ecosystem, form relationships and notice opportunities. In May 2024, he put the United States at 45 percent of Contentsquare’s business. In June 2026, he described its share as close to half. The figures belong to those moments, but the direction is clear: the move became a substantial part of the company’s development.
New York also gives the story a useful tension. He runs an international software company from an American city while continuing to describe it as French. In his public account, geographical expansion does not require forgetting the original address. Paris remains part of the working circuit, alongside New York and London. The founder’s calendar has become another kind of customer journey.
The investor who acquired a fourth baby
One of the more revealing characters in Cherki’s story is Tony Zappalà, the Highland Europe partner whose firm invested in 2016. Their relationship has produced a small domestic joke. Zappalà’s third child arrived around the time of the investment, and Cherki suggested that Contentsquare had effectively become a fourth baby. Late-night calls between New York and Geneva gave the comparison some practical force.
The joke is useful because it returns a financing relationship to human proportions. Money comes with people who answer the phone, ask awkward questions and live in other time zones. Cherki has credited Highland with understanding his concerns from their early conversations. Zappalà, for his part, has described a demanding founder willing to make measured bets, including the move to America.
“Highland backs me in the full sense of the word”
Jonathan Cherki, on his investor relationship
None of this makes the work frictionless. A close relationship can carry disagreement as well as encouragement. What the anecdote does show is the texture behind a tidy funding milestone: the investor has a family, the founder has a question, and Geneva may prefer that New York ask it earlier. Expansion is occasionally conducted in the hours when sensible people are asleep.
Buying companies, keeping a question
Acquisitions became another route to expansion. Clicktale joined in 2019. Hotjar followed in 2021, Heap in 2023. By 2024, Contentsquare had introduced an all-in-one platform bringing together its own products with those of Heap and Hotjar. The company’s story now included several teams with histories that began elsewhere.
That gives Cherki a management problem as well as a product opportunity. Buying a company adds expertise; it also adds habits, working relationships and people who remember a different beginning. A shared platform can be announced on a particular day. A shared way of working takes longer. His public discussions of growth repeatedly return to culture, learning and the people trusted to carry those ideas through an organization.
The financing figures arrived with their own scale. In July 2022, Contentsquare announced a $600 million package at a $5.6 billion valuation. The package comprised $400 million in equity and $200 million in debt. Those distinctions matter. A round is a financial arrangement at a date, with different kinds of obligations attached; it should not become a permanent adjective for the founder.
By June 2024, Cherki was openly discussing a path toward profitability. Contentsquare had also reduced its workforce by 4 percent in 2023. Including that chapter gives the growth story its proper dimensions. A company can gain products, markets and capital while still having to make uncomfortable choices about costs. For a founder who says he wants to stay for decades, those choices are part of the job.
A Marseille supporter’s management bookshelf
Cherki’s attachment to Olympique de Marseille supplies a less abstract detail. The football allegiance travels with the founder, even when the working address is New York. It is tempting to make every business decision a dressing-room speech. His reading recommendations offer a more specific view of what occupies him: leadership, difficult decisions and the human side of an organization.
On the Génération Do It Yourself podcast, he recommended Ben Horowitz’s The Hard Thing About Hard Things, Trailblazer by Marc Benioff and Monica Langley, and Hubert Joly’s book with Caroline Lambert, published in French as L’entreprise, une affaire de coeur. The shelf holds operating difficulties alongside purpose and management. Apparently a founder’s homework does not end when the diploma arrives.
His own descriptions of leadership have a student’s emphasis on learning. He speaks about recruiting people with greater expertise than his own and giving them room to work. In a June 2026 interview, he named discipline, consistency and focus as guiding principles. The aspiration to understand everything coexists with an acknowledgment that other people need to know particular things better.
“I would love to be the geek of the team.”
Jonathan Cherki, discussing specialist colleagues
That wish sounds especially telling from a chief executive. The title puts him in charge; the sentence puts him back beside the problem that interested him at school. The appeal is still the work of finding something out. There is a modest comedy in building an organization so large that your reward is the chance to keep being its curious pupil.
The customer has left the website
In July 2025, Contentsquare announced an agreement to acquire Loris AI, a conversation intelligence platform. The move extended the company’s view toward support exchanges and interactions with human and AI agents. Customers were leaving evidence in conversations as well as in clicks. Cherki’s original question had found another room in which to ask itself.
On March 17, 2026, Contentsquare announced configurable Sense Analyst agents, analytics for ChatGPT apps and prompts, visibility into traffic from large language models, and expanded conversation intelligence. The practical idea was to understand journeys moving among assistants, websites, mobile apps and support. It was a product announcement about a changing interface, rather than proof that every customer had already changed their habits.
The company’s 2026 benchmark helps keep that distinction in view. It reported a 632 percent year-on-year increase in AI-referred traffic, while placing that channel at just 0.2 percent of overall traffic in its dataset. A steep rate of growth can start from a small base. For someone fascinated by statistics, the denominator deserves as much attention as the exciting percentage.
Cherki returned to his longer commitment in June 2026, saying he hoped to remain at Contentsquare’s helm in twenty years, still learning. The future he describes is strikingly continuous. The boy expected to join a family enterprise has built another business he wants to spend his working life inside. The merchandise changed. The appetite for a long assignment survived.
There is no need to furnish that ambition with a grand exit scene. His story begins with an ordinary commercial puzzle and keeps finding versions of it: a visitor, a confusing journey, a company trying to understand. Somewhere between a banner and a basket, a student found enough unfinished work to last him much longer than a term.