He Leads A $1 Billion Cybersecurity Company Redefining The Way Enterprises Defend Against Cyber Criminals

Leadership in the fast-paced world of cybersecurity requires more than just technical expertise. It demands resilience, a strong vision, and the ability to inspire a team towards a common goal. Amitai Ratzon, the CEO of Pentera, embodies these qualities.

With a background that spans military service, a passion for basketball, and a successful career in sales, Amitai has cultivated a leadership style that is as dynamic as it is effective. His focus is on establishing a company culture that enables it to survive and thrive.

This post delves into the experiences and principles that have shaped Amitai’s journey and how they have influenced his leadership at Pentera.

Success is often viewed with rose-tinted glasses, but the journey to building and sustaining a successful venture is challenging, drawing on resilience, requiring sacrifice, and ultimately humility.

Listen to the full podcast episode and review the transcript here.

Early Years in Jerusalem

Amitai looks back at his early years in Jerusalem, Israel. Born in 1976, he had a classic 80s and 90s childhood. The oldest of four brothers, he grew up playing and following basketball, a passion he cherishes until today.

Even as a child, Amitai was totally committed to excellence and was a perfectionist student who wanted to earn perfect scores on his tests. Amitai was recruited into combat army service from Jerusalem and is very proud of his days as an officer in the IDF.

After completing his time in the army, Amitai set out to travel the world. That’s when he encountered a very interesting opportunity to be a salesman at a New York company that sold Yellow Pages advertisements to businesses across the tri-state area.

Amitai quickly rose to manage a team of 20 employees but decided that there was more to experience in his mid-20s. After working for a while, he returned to Israel to complete his studies, earning his law degree, and later, an Executive MBA degree.

He then went on to work in the sales departments of several High Tech companies, including SuperDerivatives (NASDAQ: ICE) and Earnix, his first VP of Sales position, before transitioning to entrepreneurship and joining Dr. Arik Liberzon, CTO & Co-Founder at Pentera.

Inspiration from Michael Jordan – Words to Live By

When speaking about leadership, Amitai’s inspiration stems from his love of Michael Jordan and The Last Dance documentary, which is not just about sport but also about leadership.

Playing basketball, which is an intensely competitive sport, helped shape the way Ratzon approaches his leadership position.

Michael Jordan has always been Amitai’s childhood icon and he lives by Jordan’s famous quote, “I don’t compete against others, I compete against myself yesterday.” Amitai constantly measures his progress against what he was achieving yesterday.

After years of dominating the sport, journalists would ask Jordan, why doesn’t he just take it easy and relax a bit? Jordan’s answer really left an impression on Amitai.

Jordan’s motivation to play hard for the young kid who purchased a ticket, regardless of past achievements, showcased the type of drive Amitai believed in.

Following this narrative, Ratzon feels responsible for the employees in this company, especially the newcomers who haven’t been a part of the legacy up until now. As their CEO, he feels the need to lead by example and make them feel like they are part of the journey.

He wants to inspire both the experienced Penterians and the new joiners so they continue to follow him, Pentera’s mission, and understand what the company represents.

Drawing on Perseverance to Counter the Setbacks

The four years he spent as an officer in the armed forces were instrumental in shaping the man he is today, especially when it comes to discipline. Ratzon remembers being part of the elite paratroopers Unit at the IDF and learning hard work, perseverance, & resilience.

His army experiences fostered a different perspective and helped instill in him the perseverance that he needed in his journey to become a successful business leader, drawing on it when dealing with investors, bad quarters, bad hires, work stress, or any type of business setback.

Ratzon also learned important lessons about leadership and not taking things for granted. Amitai stresses that he has never tried to lead people through seniority, but rather by setting an example.

“If you need to force someone to do something because you are more senior than they are, then, your leadership style has failed.”

Still, today, as the CEO at Pentera, he manages a very experienced leadership team, many of whom are older than him and have far more experience in their specific domains. “You don’t earn their respect and trust simply by having the title of CEO; it needs to be more than that.”

Amitai stresses that he has worked to gain their support and trust, striving to work the hardest, securing their buy-in through leadership by example.

Learning the Different Roles to Become a Successful CEO

Israel is a great supplier to the world of cybersecurity companies, and the CEO profile within the cybersecurity ecosystem tends to be fairly homogeneous. Only 2% to 3% of CEOs in this space in Israel have similar backgrounds to Amitai’s combat background.

Instead, most cybersecurity CEOs in the Israeli ecosystem matriculate from a select group of intelligence or technology units. “They bring a cybersecurity background to the CEO position; they are technologists who transition to become CEOs leading a business.”

In Amitai’s opinion, there’s a lot more to being the CEO of a company than coming up with a great technological idea and building a product.

He considers the skill set needed to build the first product and reach the 10-customer milestone to be very different from what it takes to continuously manage a larger, more established company.

Having both skill sets is rare and only a select group of gifted individuals have managed the transition from product development to CEO well.

For Amitai, as a two-time former VP of sales with vast go-to-market experience, stepping into the CEO position was a natural step.

He had previous experience dealing with board members and the responsibility to look after the company’s numbers which he believes translate very well in the CEO role.

Most Israeli startups are founded by technologists who eventually transition to become CEO as the company grows; their skill sets are more naturally based on the technological development side, and they have a limited background in business development to draw from.

While Amitai previously worked alongside CTOs, Heads of Marketing, and Heads of Finance, often as a sales leader, they never reported to him. Stepping into the role of CEO and having all the functions beneath him, Ratzon took the opportunity to learn everything he could.

He had to be very humble as he learned about running functions that he previously knew very little about. Amitai says he learned a lot about R&D, how engineers think, and what motivates and inspires them.

He gained firsthand experience in what it means to lead marketing from the top, a shift from his previous role where he worked in parallel with the marketing department.

He also immersed himself in the G&A functions, finance, and legal, absorbing as much knowledge as possible and taking the opportunity to ask as many questions as possible along the way.

Meeting His Co-Founders and Taking Pentera Out of Stealth Mode

Following his successful tenure as a VP of Sales, Amitai ultimately met with the people who would become his partners at Pentera.

He was introduced to Dr. Arik Liberzon, Pentera’s co-founder and CTO, in 2017 by Arik’s Co-founder, Arik Faingold, as well as the company’s early investors, AWZ Ventures. Amitai holds deep respect for Arik Liberzon, who he claims had the rare insight to take on the position of CTO and not CEO.

Arik understood from the beginning that his passion was the technology and product vision; combining Arik’s expertise in technology and product development with Amitai’s strong Go-to-Market expertise has resulted in a highly effective partnership that has allowed both partners as well as the company to thrive.

Amitai acknowledges that in the technical space of cybersecurity, his success relies on having a strong partner like Arik to manage the technical and product vision, while he manages the business.

“Arik was definitely the perfect partner as he is the technological visionary, but was also humble enough to allow someone else to become the CEO of his idea. Not every founder is able to give that up.”

The Building Blocks for Success at Pentera

As with any venture, the journey started with a vision and a dream. “Everyone thinks that their product can be the next biggest thing out of the Israeli cyber market. You have to believe that strongly to get anywhere.” Once we had the vision, we started recruiting the team.

Everyone started recruiting the best people they’d worked with in the past. Arik quickly brought in Ran Tamir, as the Chief Product Officer, and Alex Spivakovsky, as the VP of research.

Amitai brought in Aviv Cohen as CMO and Sivan Harel as the first salesperson on the ground to run big parts of Europe, after working together with both at a previous company. Harel has grown with the company and is now the VP of sales in EMEA.

As Amitai explains, they hired who they could trust and these people brought in more people until they built a cluster team of 30 to 40 members, most of whom are still with the company today as VPs.

Together, they became the core team of Pentera and their camaraderie, determination, and conviction have taken it where it is today. The company has been built for success and recently surpassed 1,000 global customers.

Rounds of Funding at Pentera

Pentera is very famous in the VC world as a company that didn’t miss a quarter for 24 straight quarters; an impressive achievement for an early-stage, privately held company.

Amitai, Arik, and the core team have taken Pentera through a few funding rounds and have raised more than $120M (with more deals between shareholders that happened in parallel). But while raising money can be a great experience, Amitai advises caution.

Storytelling is everything that Amitai Ratzon was able to master. Being able to capture the essence of what you are doing in 15 to 20 slides is the key. For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) where the most critical slides are highlighted.

Remember to unlock the pitch deck template that is being used by founders around the world to raise millions below.

“One tip I would give to aspiring entrepreneurs is to be extremely cautious about the investors you partner with.

When you’re in the process of raising money, people will shower you with compliments to get into your world. Some may even give you offers and these may be very tempting. Taking the money too fast can become an issue if you bring the wrong people into the family.”

The leadership team at Pentera is very happy with all of their investor choices, but speaking to other CEOs, Amitai has heard some challenging stories.

Eventually, investors become a part of the core cluster group, that’s something to be aware of since people have different motives and agendas.

What usually doesn’t change is the DNA of the human beings you are working with that sit on your board. Pay attention to the personas that are sitting on your board. Are they placing partners or GPs on your board, or someone more junior?

This can indicate the level of conviction that they hold in your company as an investment.

Challenging the Paradigm

Amitai challenges two misconceptions prevalent in the entrepreneurial world. The first is that you need to have a certain background to succeed in the cybersecurity market, as a founder/CEO.

“Most VCs looking at the cybersecurity landscape in Israel tend to invest in founders from specific army units, who are within a certain age range. That has been the template, but the reality is that many of those companies don’t make it beyond Round A.”

Pentera was built with a different DNA, having a very experienced C-Suite who knew how to succeed and did not meet in the army at the age of 18, but rather spent lots of time at B2B Hi-Tech companies, amassing a ton of experience and exposure.

The second concept that Amitai challenges is how many VCs view the market. In his experience, many of the VCs consider the US to be “the world”, and “the rest is the rest.”

While Ratzon acknowledges the strength of the US market, he hasn’t allowed it to become the singular focus of Pentera. As Amitai sees it, the US is the single biggest market and probably represents the biggest kind of gift to any founder that wants to become a global company.

However, with that said they should also be open to attractive territories like the UK, Germany, Spain, France, Italy, and others.

While it might be too much for most start ups to target this many regions from the beginning, as you transition to become a bigger company between Round A and Round B, you should start diversifying your regions.

In Amitai’s experience being completely dependent on the US, its buying dynamics, and economy alone is not advisable. Today, Pentera has a presence in 18 countries and over 1,000 customers from 64 countries. Pentera is very much an international business.

Amitai’s Future Vision for Pentera

Amitai’s ultimate vision will likely materialize in four to six years because it takes time for companies like Pentera to become mainstream and the brand everyone recognizes.

Amitai wants Pentera to be a ubiquitous brand that stands for quality like having the Intel or Pentium sticker on your laptop.

Amitai envisions a world where Pentera is used by 3,000 to 4,000 customers worldwide and is present in every big bank, healthcare, government institution, or manufacturing company. Ratzon wants to see most Fortune 500 companies being in a position where they are protected by Pentera.

Like seeing the Pentium or Intel stickers on almost all laptops, Amitai envisions a Pentera “virtual sticker” that will be equally prolific, representing cybersecurity excellence and serving as a deterrent to hackers who understand the security resilience that entails.

Lessons for Aspiring Entrepreneurs

The first piece of advice is to be “all-in” and the second piece of advice is to make sure that you have the support to back you up in difficult times.

While the younger generations are putting greater emphasis on work-life balance, and there is value in that, there are no shortcuts. To succeed as leaders of the company and for the venture to succeed, you will have to invest and make large sacrifices of your time to attain the peaks.

If your attitude is “this is just a job” that’s great, but then, don’t start a business with high expectations for success.

Pentera achieved a $1B valuation in 2021, but that was the result of many people making the company their number one priority in life.

“I would love to say that my wife and children always came first, but there were many situations where they came second and you need to have a very supportive home to do that.

”You can be as talented as anyone, but if your family and support system don’t give you the backing, then, it’s very difficult.

There will be times when you go through a frustrating business trip, a frustrating investor dynamic, or when something doesn’t go well with your co-founders. At that time, you will need someone there who believes in you, irrespective of how quarter A or quarter B turned out.

As a CEO you rarely get that unconditional support. People meet with you all the time in the business, but it’s always because they want or need something from you. You need someone from the outside who believes in you and sticks with you through good and bad, without an “agenda.”

“My wife, Dafna, has been this person for me since always and as much as she’s my number one fan, I’m hers as well.”

Conclusion

Amitai Ratzon’s journey from the basketball court to the battlefield, and ultimately to the boardroom, has shaped him into a leader who is both resilient and empathetic.

His experiences have taught him the value of culture, the importance of teamwork, and the necessity of being adaptable in the face of challenges. At Pentera, these lessons have translated into a thriving company that is well-positioned to tackle the evolving challenges of cybersecurity.

Listen to the full podcast episode to know more, including:

• Leadership is about more than making decisions; it’s about building a cohesive team and earning the respect of those you lead by example
• There are no shortcuts. Leadership requires significant sacrifices, but these challenges build resilience and empathy.
• A strong, positive culture is the backbone of a successful organization.
• Have a strong support system to back you through good and bad
• Lessons from basketball or any competitive sports, like teamwork and perseverance, are crucial for effective leadership.
• Military experience teaches discipline, strategic thinking, and calmness under pressure—vital traits for a CEO.
• A customer-centric approach, honed in sales, is essential for driving business success as a CEO.
• Resilience in the face of adversity is key to thriving in the fast-paced cybersecurity industry.

 

SUBSCRIBE ON:

For a winning deck, see the commentary on a pitch deck from an Uber competitor that has raised over $400M (see it here). 

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.