5 Insights from a Unicorn CEO

Kyle O'Brien
Revaia Voice
Published in
7 min readJul 22, 2022

Key Takeaways from a Conversation with Contentsquare CEO Jonathan Cherki

Contentsquare CEO, Jonathan Cherki (Source: Contentsquare)

A couple of weeks ago, we gathered with LPs and Founders in Chamonix for our very first Portfolio Days event — if you missed it, we covered it in detail in this recent post. Among the many activities, we hosted several panel discussions and Q&As as a way to learn and share among peers as well as industry leaders. During one of those sessions, it was our great privilege to welcome Jonathan Cherki, Founder & CEO of Contentsquare, to share his perspective on scaling what would become a “unicorn” company, international expansion, culture & identity, and maintaining integrity and conviction throughout the journey. For the sake of confidentiality and open dialogue, we didn’t record the meeting. The team at Revaia, however, took some mental notes that we’ve translated into 5 Key Insights from a Unicorn CEO.

Here are each of the insights in shorthand:

  • Always Be Closing (Demo-ing)
  • Test, Iterate, Learn, Repeat
  • Allow Individual Cultures to Flourish… But Build a Bridge
  • To be a Market Leader, You Have to Set an Example
  • Day One Convictions Matter

#1: Always Be Closing (Demo-ing)

Alec Baldwin in 1992 film (and Sales Masterclass) Glenngary Glen Ross

Not five minutes into the Q&A, Jonathan polled the crowd on who might be interested in seeing a demo of the latest and greatest the Contentsquare platform has to offer. The response: a resounding yes! We weren’t just getting a demo from the CEO (and consummate salesman), but unique insight into the vision and direction of a global company that is firing on all cylinders. At a startup, building a “sales machine” is critical, especially in the world of B2B SaaS. It requires discipline, playbooks, demo assets and persistence — and typically, that very first salesperson in the founder.

CEOs tend to differ in backgrounds, and various traits have gained favor in across eras: the 80s saw former CFOs take the top spot, the 90s ushered in the era of former CMOs, the 2000’s was Product & Design oriented and today there’s arguably a competitive advantage with CEOs who understand supply chain. Despite the skill set variance of those in charge, there’s one thing that has remained constant: selling. Jonathan is a Salesman at heart and his presentation was second to none as far as live software demos go. You might think: what’s the big deal… it’s just a demo? In the top spot, it’s easier to lose touch with the day-to-day than you might think. Jonathan’s knowledge of granular details paired with visionary thinking is a unique blend that sets an example from the top down. Consistency, clear messaging and delivery are key from top to bottom of the organization and he exemplified this rarified skill as a world class CEO.

#2: Test, Iterate, Learn, Repeat

The common startup wisdom tends to sound cliché. But I would argue that common sayings become cliché because they are so true. Things like “Fail Fast” and “Pivot to Product-Market Fit” seem obvious, but they require concerted effort and intentional frameworks. This holds true for processes across each vertical within an organization: international expansion, acquisition strategy, and hiring.

An example of a Startup-ism from Facebook that happens to run counter to the French startup philosophy of building with intention (i.e. without breaking things!)

International Expansion

For most companies with global ambitions, penetrating the US market is a part of the long-term strategy. The Contentsquare team took advantage of a proxy — the UK — to test out their go-to-market strategy in an English-native territory with non-trivial cultural differences. By landing and expanding in London, they were able to learn from any unexpected pitfalls, refine their English-language marketing content and build the content assets necessary to build a sales machine. It served as a launching pad for their eventual move into the US via New York City.

A History of Contentsquare (Source: Contentsquare Blog)

Acquisition Strategy

At any given time, there are hundreds of probable acquisition targets. Simultaneously, there are several acquisition rationales: product, team, synergy or parallel markets. To date, Contentsquare has made 6 acquisitions, each of which have delivered different value to the overall product and growth strategy. The lesson from Jonathan is that in all cases, regardless of rationale, it’s the people that matter. Trust in high quality people and a lot of the rest falls into place.

The Cherki Ratio (Source: Startup ROI)

Hiring

Employee success and recruiting has become a critical subject in the past several years. Attracting the best talent and maximizing retention is necessary for a company to achieve and maintain momentum. From 1 to over 1K employees, Jonathan has tested, iterated and learned quite a bit, so much so that he’s distilled it into a formula. An attractive talent market optimizes for Quality/Price multiplied by Loyalty. A standard example: the US versus the French market. Both regions have high quality developers and sales people, but the cost is much higher in the US. In addition, due to contract law, culture and opportunism, US employees tend to be less loyal, meaning they get poached by recruiters or move to the next best thing at a moment’s notice. Part of the reason Contentsquare has retained its core R&D hub in France (and Israel!) is based on this core tenet of his hiring model.

#3: Allow Individual Cultures to Flourish… But Build a Bridge

You would think after building a strong company culture “at home” that you could just copy & paste said culture when opening new markets. Unfortunately, that’s not the case. Basic obstacles like language barriers and time zones are inevitable, but deeper-seated complexities like regional politics, team dynamics, communication strategy and unified messaging can be very difficult. There are a few best practices that Contentsquare adheres to: sending “ambassadors” from HQ to open new offices, a heavy emphasis on A-players for the first 50 employees in a new hub and regular all-hands meetings to promote open communication and transparency. But ultimately, each hub will have its own identity and it’s important to foster this while facilitating cross-cultural exchange. There’s no formula here, but Jonathan’s words of wisdom: remain open-minded, flexible and make sure to listen.

#4: To be a Market Leader, You Have to Set an Example

This may sound like the advice of a parent to their eldest child. It holds true in business, too. Being a market leader is more than just hitting revenue targets and taking market share. You have to set the tone for your entire industry through product delight, customer success and perhaps most of all initiatives for the betterment of your industry, above and beyond the requirements of your business. A clear leader in these philanthropic efforts is Salesforce and their 1:1:1 model — donating 1% of employee time, equity, and revenue to charity. Following in their footsteps, Contentsquare has built a foundation around internet accessibility, a genuine, yet underrepresented, problem of the modern era. The foundation conducts science and research, builds solutions and provides accessibility education and training at scale. They aren’t just leading the market, but setting the example.

Some startling statistics on accessibility the Foundation aims to solve (Source: Contentsquare)

#5: Day One Convictions Matter

From the very beginning, Jonathan set his sights on becoming a global brand, setting the organization up to become an “institution” among top technology companies. This has been clear since day one. During his presentation, he shared an anecdote about the family business. His grandfather started a vegetable import/export operation about 70 years ago. His father eventually took over. To Jonathan, loyalty and commitment are paramount. Despite running a multinational corporation, he treats it like a family-run operation in the sense that he takes accountability and plans to run it for the rest of his career. This mindset has been baked into the company DNA and has contributed to strategy and operational excellence from the earliest of days.

It was a pleasure to welcome Jonathan Cherki to our very first Portfolio Days event. At the time of writing this, Contentsquare announced a $600M Series F, doubling the company’s valuation to $5.6B. A big congratulations to Jonathan & team!

$600M Series F Announcement (Source: Contentsquare Blog)

Kyle O'Brien

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Kyle O'Brien
Revaia Voice

Operating Partner @ Revaia / Founder @ Startup ROI