CEO Insights: Mastering High-Stakes Leadership in the iGaming Sector

The gambling sector has always been a very profitable one, dating all the way back to when the first land-based casinos started appearing. Online gambling made starting a casino easier than ever, making it possible for entrepreneurs to open casinos without having to put millions of dollars on the line. Having a competent CEO has always been important, but this importance is even more noticeable when it comes to the iGaming sector.

CEO Insights: Mastering High-Stakes Leadership in the iGaming Sector

However, this opportunity did not go unnoticed by most. According to, there are hundreds of online casinos that cater exclusively to high-value customers. When you consider all the other internet-based casinos, the number quickly goes to the dozens of thousands.

But how can an online casino distinguish itself from the competition? In this article, we will look at how CEOs can influence gambling companies, and what key characteristics are common among the top gambling CEOs.

Profiles of Top High Stakes iGaming CEOs

While managing an online casino is always going to be a difficult and complicated task, that difficulty gets exponentially higher as the user base starts expanding and including high-value customers. For that reason, and even though they are both difficult jobs, managing a regular online casino is not going to be as difficult as managing a high-stakes one.

Gambling CEOs are aware of these differences. But, while a high-stakes leadership position is within the reach of most iGaming executives, there are a few key leadership qualities that boardrooms look for when considering the company’s next CEO.

But what are they? Let’s take a look at the profiles of some of the more influential gambling CEOs to find out.

1. Jason Robins – DraftKings

Jason Robins co-founded DraftKings in 2011 and assumed the CEO position ever since. In 2020, he expanded his control within the company, becoming Chairman of the Board as well.

As CEO, Jason Robins not only oversees the company’s day-to-day operations, but also drives its strategy, financial investments, and other initiatives.

But what key qualities does the popular sportsbook’s CEO have? Among other things, Mr. Robins has always been a forward-thinker with an eye for investment opportunities and a pendant for strategic leadership. This helped him and his company pass key regulations regarding sports betting and fantasy sports, which in turn made DraftKings a very valuable betting platform.

2. Ashkenazi Rafi – The Stars Group (Flutter Entertainment)

Rafi Ashkenazi has been the CEO of The Stars Group since 2016. His seven-year tenure was very important to consolidate and solidify the TSG’s position in the online gambling market.

Rafi’s key characteristics are his hands-on approach to leadership, as well as a strategic approach to gambler’s needs and desires.

3. Jesper Svensson – Betsson Group

Jesper Svensson hasn’t been Betsson’s CEO for very long, however, his short tenure has already achieved massive financial success. In just 12 short months, Betsson’s stock surged 52%.

Before assuming the group’s CEO position, Svensson acted as Betsson’s Malta CEO for four months. Svensson is a leader who focuses on connecting with the employees, and fostering a cohesive, diverse, and inclusive workspace.

4. Per Eriksson – NetEnt (Evolution Gaming)

Per Eriksson was NetEnt’s CEO for 6 years. He led the company into new markets and oversaw the biggest expansion of the company’s portfolio in NetEnt’s history.

He has been the CEO of 8 other companies and holds an MBA from the University of Stockholm. Per Eriksson is a hard worker and a very dedicated executive officer.

5. Philip Bowcock – William Hill (Caesars Entertainment)

Philip Bowcock was William’s Hill CEO for 3 years. He first joined the company as a Chief Financial Officer but quickly managed to climb the executive ranks.

During his tenure, Philip had to deal with the government’s crackdown on sports betting, which proved itself to be a very difficult task. As a CEO Philip Bowcock proved himself to be resilient and very determined.

Key Strategies of High-Stakes CEOs in iGaming

CEOs can have very different leadership styles. Often, iGaming companies have to navigate complicated laws and regulations whenever they tap into a new market, and there is no set leadership style that is better suited to handle these complicated and sensitive matters.

As we have seen in our brief CEO overview, these executives faced different types of situations, and some of them did not manage to stick with the company after their endeavors.

But what are the key strategies that these CEOs can use to influence gambling companies? Let’s find out.

Strategic Market Entry and Expansion

Did you know that not every country allows online gambling? There are still lots of untapped markets and a lot of profit to be had. CEOs oversee market entry and deal with policymakers, lobbying to alter gambling laws and regulations.

However, they don’t do it based on feeling. These strategies are always accompanied by extensive studies and market analysis. Being a CEO requires a strategy-focused mind.

Customer-Centric Approaches

When it comes to iGaming, clients make or break entire companies. The competition is fierce, and gamblers have limited time and budgets.

For that reason, CEOs have to focus on fostering their customer relations too. Otherwise, gamblers will just choose a different gambling website to spend their hard-earned dollars on.

Technology and Innovation

The iGaming field is constantly innovating, following trends and new technologies. For that reason, gambling companies often prefer younger and more tech-savvy CEOs.

Gambling companies need to use technology to enhance user experience if they wish to remain competitive, otherwise, they will be surpassed by other companies that do so.

Talent Acquisition and Leadership Development

A happy and cohesive team is essential for any company to thrive. iGaming CEOs need to foster good working environments to hold on to their best employees, which in turn allows the company to succeed.

Adaptation to Changing Consumer Trends

Because of new technologies and other innovations, consumer trends are always evolving. Besides adapting to new technologies, companies also need to adapt to their customer’s needs and desires if they wish to be successful.

Good CEOs know this and make market research one of their top priorities.

Conclusion and Final Thoughts

Being a CEO is more difficult than some people might think. CEOs need to have key leadership qualities that are specific to the gambling sector if they wish to master high-stakes environments.

Besides having a strategic mindset, CEOs also need to know how to foster a good workplace and how to approach their customers’ needs, while expanding and bettering the company’s portfolios and services.

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