The future of iGaming leadership: What boards and investors expect in 2026

What does effective iGaming leadership actually look like in 2026? And as the industry matures, regulates, and begins to grapple with AI, how are the demands on senior executives changing?

These are the questions at the centre of Episode 19 of the podcast Connected with Pragmatic Solutions, in which CEO Ashley Lang speaks with Andrew Bulloss, Partner and Head of Global Gaming Practice at Odgers. With over 16 years specialising in senior executive search across the gaming and gambling industry, Bulloss has a direct line of sight into how boards, investors, and founders are thinking about leadership today.

From hustle to structured leadership

The iGaming industry built itself on speed and entrepreneurialism. A decade ago, the profile of a successful operator leader was often defined by founder energy: high risk tolerance, fast decision-making, and a willingness to operate in uncharted territory. That profile has not disappeared, but it has been substantially supplemented.

Today's regulated, multi-jurisdictional environment demands a different kind of leader. Boards operating in licensed markets want executives who can grow a business responsibly and demonstrate that responsibility to regulators, investors, and the public. The weight of reputational risk is now a standing item on most board agendas, and leaders are expected to bring rigour and discipline alongside commercial ambition.

The command-and-control style common in iGaming leadership ten years ago is increasingly giving way to something more self-aware. Emotional intelligence, humility, and data-led decision-making are now consistent requirements in senior briefs, whether the business is a scale-up or a listed operator.

Matching the leader to the stage of the business

One of the clearest themes from the conversation is that leadership requirements are not fixed. The skills needed to take a business from series B to series C are not the same as those required to run a mature, multi-market operator. The question Bulloss and his team ask from the outset is not simply what the role requires, but what stage the business is at and what challenges it faces next.

Is the organisation moving from a single-product to a multi-product model? Expanding from one regulated market into several? Managing a founder transition? Each of these scenarios calls for a different weighting of the same core traits. The ability to identify that distinction, and hire accordingly, is one of the more underappreciated aspects of senior recruitment.

For operators using the Pragmatic Solutions PAM platform to support their expansion into new markets and jurisdictions, this question is directly relevant. The technology infrastructure can scale. Whether the leadership team can scale with it is a separate question.

The B2B versus B2C distinction

Bulloss draws a clear line between the skills required to lead a B2B business and those needed for a B2C operator, while also identifying what the two have in common. Both require strategic thinking, the ability to set a vision, and strong people leadership. Both require a customer-first orientation, even if the customer in question is an operator rather than a player.

Where they diverge is in team composition and commercial emphasis. A B2C operator needs depth in CRM, marketing, and data. A B2B provider needs strength in business development, customer success, and product. The core leadership traits remain consistent; the weighting of functional expertise differs.

AI and the evolving executive brief

AI has moved slowly onto iGaming executive job specifications. According to Bulloss, it is only in the last nine months that AI fluency has appeared in senior briefs for roles other than CTO, and it is still more often listed as a preference than a hard requirement. That is beginning to change.

Larger operators are primarily applying AI to internal productivity and operational efficiency. Smaller, AI-native businesses are using it to build externally facing products and propositions, partly because they carry less legacy technology. The leaders who are handling this well are those who are selective about where they invest their AI focus: identifying specific projects, building small dedicated teams, and measuring outcomes.

Bulloss notes that two briefs taken in the same week, one for a chief product officer in a B2C operator and one for a CEO in a B2B business, both explicitly listed AI capability within the top four requirements. That would not have been the case six months prior.

For operators who are also thinking about how to structure their technology and data capabilities as AI becomes more central to operations, the Pragmatic Solutions Data Lake and Integration Hub provide the infrastructure to support those ambitions.

Bringing talent in from outside the industry

The iGaming industry has a well-documented retention problem in reverse: people rarely leave. But for specific functional areas, such as finance, technology, HR, and legal, out-of-sector appointments can work well. The challenge is in execution. Organisations that fail with external hires typically do so not because the individual lacks ability, but because the business does not create the conditions for them to succeed.

Industry-specific knowledge, including terminology, regulatory context, and commercial norms, takes time to acquire. Bulloss argues that businesses should anticipate this gap and build it into their onboarding process, rather than treating ignorance of iGaming-specific conventions as a mark against the individual. The organisations most likely to attract strong external talent are those that can demonstrate clear values, a credible regulatory posture, and a leadership team worth joining.

What it takes to make the step to C-suite

For those not yet at senior executive level, Bulloss offers three practical steps. First, find a mentor who has been on a comparable journey and can provide honest, contextually relevant guidance. Second, seek out board-level exposure, whether through a non-executive appointment, a trustee role, or a board advisory position, in order to understand how decisions are made at that level. Third, ask for genuine feedback from the people who matter, including those who may not hold a favourable view, and choose one specific thing to change.

The broader theme throughout is preparation and self-awareness. Candidates who arrive at senior interviews with a considered opinion on the business, even an imperfect one, are consistently valued over those who simply present their own credentials.

5 key takeaways

• Leadership demands in iGaming have shifted from hustle and speed to a balance of commercial drive, emotional intelligence, and regulatory rigour.

• The right leader for a business depends as much on the stage and challenge the organisation is facing as it does on the individual's experience. Hiring for the next phase is the critical skill.

• AI is beginning to appear in senior executive briefs in iGaming. Boards and investors are starting to ask how AI-fluent a candidate is, and that question is intensifying.

• Out-of-sector hires can add real value in functional roles, but they succeed or fail based on the quality of the onboarding. Industry knowledge gaps are predictable and should be planned for.

• Aspiring C-suite executives should not wait for the role to arrive. Finding a mentor, gaining board exposure, and actively seeking critical feedback are all actions that can be taken now.

  
  

Watch the full episode here