October 2016

Highland Team:


Fully-automated Saas digital experience insights platform

he Manhattan view from the window behind Jonathan Cherki’s desk seems appropriate considering the dizzying heights of ambition that the founder and chief executive officer of Contentsquare has demonstrated over the past few years.

In 2012, he launched Contentsquare, an e-commerce optimisation site, in Paris. Since then, it’s become a global leader in digital experience analytics. Its US office, perched 54 floors above New York City, is clearly one of many testaments to that remarkable journey.

Jonathan Cherki, CEO & Founder of Contentsquare and Shlomi Hagai, CEO of Clicktale. Contentsquare acquired Clicktale in July 2019.

Jonathan Cherki, CEO & Founder of Contentsquare and Shlomi Hagai, CEO of Clicktale. Contentsquare acquired Clicktale in July 2019.

Tony Zappalà, partner at Highland Europe, attributes much of Contentsquare’s success to Jonathan. “He’s someone who breaks through walls to get things done,” Tony explains. And Jonathan reciprocates the praise by acknowledging that Tony was “one of the first to really believe in me and Contentsquare.”

From the first contact between the two in May 2016, Jonathan elaborates, Tony and his team “understood my points and my fears.” And, he adds, there was never a case of something not being possible: “Highland backs me in the full sense of the word and it’s this belief that makes me want to keep working with them.”

Highland backs me in the full sense of the word
— Jonathan Cherki, Contentsquare CEO & Founder

Naturally, when stakes and passions are high, tensions can materialise. Jonathan’s move to the US in 2017 was an inflection point and a huge bet on a fast-growing market, but Tony is adamant that bold moves – an ability to make measured risks – is what has helped Contentsquare to distinguish itself.

Tony also values Jonathan’s ambition and the fact that he’s “one of the most demanding CEOs – in the best possible way.”

The professional success of Contentsquare has also cemented the personal relationship between Jonathan and Tony. Late night calls from New York to Geneva have become a frequent occurrence and Tony’s wife and children graciously accept them as a necessity.

In fact, the Zappalàs welcomed their third child in October 2016, just around the time of Highland’s investment in Contentsquare. Jonathan jokes that in some senses his business became Tony’s fourth baby. “It’s certainly growing as fast as a newborn would,” admits Tony. “But I actually get more calls at night from Jonathan than from any of my actual kids!”

Contentsquare’s technology is unique because it focuses on understanding and improving customer experience, as opposed to focusing solely on customer acquisition.
— Tony, Partner

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