After five and a half years of driving success at Digitain and SportGenerate and over 15 years in the iGaming industry, Simon Westbury decided to take a career break in October 2024. It’s a pivotal moment for reflection – an opportunity to look back, analyze his journey, and chart the path forward.
SBC Eurasia sat down with Simon to ask 10 key career questions, offering an inside look at the milestones that shaped his remarkable career and the principles that have made him a standout leader in the iGaming world.
– What was your first job and what led you to pursue a career in the iGaming industry?
– My first job was as a shop assistant in a stationery store. At the time, I had decided to take a gap year after achieving better-than-expected exam results, which allowed me to apply to a different university.
My journey into the iGaming industry began in 2008 when I organized the Gaming Executive Summit (GES). The people, the energy, and the atmosphere of the conference were unlike anything I’d experienced while organizing other events. The industry was exciting, and I wanted to be part of it.
– What was the single biggest turning point in your career?
– The biggest turning point has to be when I was asked to organize the GES at very short notice after a colleague unexpectedly resigned. Within just two hours of being assigned the conference, I was already in a meeting with Deutsche Bank, the main sponsor, which meant I had a crash course between bricks-and-mortar and online. If my colleague hadn’t resigned, I might never have found my way into this field.
– What have been the biggest challenges you’ve faced in your career, and how did you overcome them?
– There’s a saying: ‘10% of conflict is due to a difference in opinion, and 90% is due to delivery and tone of voice.’ I’m naturally direct and honest, which can sometimes clash with different cultural expectations. Over time, I’ve learned to focus on the delivery of my message. My wife often reminds me that while I’m usually right on work-related topics, my delivery can sometimes hold me back.
– Who has been the key mentor in your career, and what is the best piece of advice you ever received that still drives your work today?
– My key and truly my only mentor is Roger Withers. He’s been a constant source of inspiration, always there to celebrate successes and offer advice when needed. He told me not long ago he was proud of me and what I achieved at Digitain Group. Hearing those words from someone who has achieved so much in his career was incredibly humbling. The best piece of advice came from Roger, when during Playtech board meetings, he adapted the Nike slogan of ‘Just do it’, to ‘Just f**king do it.’
– What advice would you offer to those just beginning their journey in the industry?
– I would say always act with integrity and put the goals of the company you’re working for over your own personal ambitions. If you work hard, trust your instincts, and show both flair and determination, you will do well. I would also emphasize the importance of honesty, but remind people to be mindful of how that honesty is delivered. Finally, I would say: focus on the job itself, not the job title.
– You’ve seen the iGaming industry evolve over the years. What are the biggest changes you’ve witnessed, and where do you think the industry is heading next?
– The biggest changes I’ve witnessed are undoubtedly related to regulation. When I started, there was little to no regulation for online gaming in markets like the UK, and Italy was just beginning to explore regulatory frameworks. This means the industry has matured, and we have grown up as an industry in many ways.
– You’ve made bold moves throughout your career. Do you have a personal mantra or philosophy that guides your professional decisions?
– Yes, I’ve taken some bold chances throughout my career, but through hard work and determination, I’ve managed to turn every move into a success. My philosophy is rooted in two key ideas: trusting my instincts and building momentum.
Momentum, in particular, is intrinsic to everything—whether it’s sales, product development, or overall company success. It’s tough to build at the start, but once you get it going, the snowball effect kicks in, and everything accelerates from there.
I also believe success is never a one-time achievement. You’re only successful at the moment of success—for example, signing a contract might feel like a win, but the real challenge is delivering on it. And once that’s done, it’s about nurturing the partnership to grow that success further. To me, momentum and success are continuous processes, and you need an insatiable drive to keep pushing forward.
– What accomplishment in your career are you most proud of, and why does it stand out to you?
– The biggest accomplishment to me was building the sales team at Digitain. Between 2020 and 2023, the numbers we achieved were unmatched and continue to account for the majority of the company’s revenue today.
However, to me, the main accomplishment was developing the team. Those who remained with Digitain Group have all earned promotions, with some even rising to C-level, and those who left all went to Tier 1 gaming providers. Seeing the growth of those team members is my biggest accomplishment.
– iGaming is known for its fast-paced and innovative environment. How do you stay inspired and maintain your creativity amidst the industry’s rapid evolution?
– This has changed for me. Early on, my motivation was simple: close the next sale, earn more commission, and keep pushing forward. Climbing the corporate ladder wasn’t something I actively pursued — I just worked hard without a set plan. Now, my passion lies in working with, developing, and learning from my colleagues as a manager. Nothing gives me more motivation than seeing those I have worked with succeed.
– Looking back, is there anything you would have done differently in your career? What lessons have you learned from any missteps or regrets?
– I wouldn’t say I have regrets, but in hindsight, there are things I could have done differently. As I’ve mentioned, delivery is something I work on constantly. I’ve also sometimes prioritized loyalty to the company I work for over personal benefit, which has occasionally impacted my career progression. There are two instances where I turned down unsolicited job offers because of my commitment to the company I was with, even though my instincts were telling me it might be time to move on.
That said, we all follow our unique path. As long as you keep moving forward, you’re making progress. Progress equals momentum, and that’s a lesson I always remind myself of.
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