In this episode of iGaming Leader, Leo sits down with Simon Pilkington, former CEO of Catena Media and experienced iGaming executive.

Simon shares his transformative journey, from navigating imposter syndrome and career shifts to prioritizing his health and well-being.

They go deep into leadership challenges, personal growth, and the power of building a strong support system.

Simon shares some valuable insights and practical advice for leaders striving to balance career success with personal fulfillment.

Guest Bio

Simon Pilkington is a seasoned iGaming executive with a background in leadership, strategy, and business transformation.

17+ years in the iGaming industry, spanning operator, media and data companies, affiliate companies, and his own businesses.

Not a 'straight forward' career path, but one that led to CEO leadership with KaFe Rocks. Currently running Wander, a specialist and unique recruitment business, alongside a start-up and bootstrapped affiliate company called Best Betting Media.

Key Topics Discussed

00:00 – Taking over as CEO: The challenges of stepping into leadership
05:42 – Overcoming imposter syndrome and self-doubt
09:58 – Balancing career, family, and well-being during the pandemic
11:36 – Transforming health: From burnout to peak performance
17:08 – The power of delegation and trusting your team
22:11 – Lessons from leadership: Building the right company culture
26:25 – Getting out of your own head
34:28 – Simon’s charity work: From boxing to running 180 miles for a cause

Memorable Quotes

"I was doing everything for everyone—except myself. When I finally prioritized my well-being, everything else improved."
"You don’t get rid of imposter syndrome—you learn to manage it and use it to your advantage."
"Leadership isn’t about knowing everything; it’s about surrounding yourself with the right people and trusting them."

Important Links

• Connect with Simon Pilkington:
  • https://www.linkedin.com/in/simonpilkington
  • https://www.wearewander.co.uk
• Support Simon’s charity run: https://www.justgiving.com/page/olivers-army-6-ultras

• Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/
• Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup
• Join the iGaming Leader Mastermind: https://www.igamingleader.com/

In this episode of iGaming Leader, Leo sits down with Britt Boeskov, an experienced executive in iGaming and digital transformation.

Britt shares her journey from starting as a management trainee to becoming a C-level leader in a fast-paced and highly regulated industry. The conversation explores career progression, leadership challenges, the power of building strong professional relationships, and the impact of AI and personalization in the gaming industry. Offering valuable insights, Britt provides actionable advice for professionals looking to step up in their careers and lead with confidence.

Guest Bio

With 20 years of experience in the i-gaming industry, Britt is a board member and advisor who specialises in strategy, customer experience, and digital transformation.

After a long C-level run with Kindred Group, she now serves on the boards of Better Collective, Mindway AI, GAMING1 Group, MAG Interactive and Racecourse Media Group; and provides tailored support through 4see Advice.

Key Topics Discussed

02:00 – Britt’s journey to C-level executive

04:40 – Transitioning to an established industry leader
07:00 – Stepping into leadership: Taking ownership and leading with confidence
09:50 – Sometimes you just have to take the corner office
11:20 – You don’t have to do it all yourself
16:00 – The importance of delegation and trusting your team
21:20 – Finding purpose in leadership and the role of responsible gaming
24:50 – The evolution of player engagement and the role of AI in gaming
29:30 – Britt’s advice for leveling up your career

Memorable Quotes

"You don't get the corner office. You take the corner office."
"High performers balance humility and curiosity with ambition and persistence."
"The one lasting thing you build in this industry is your relationships—hold on to them."

Important Links

Connect with Britt:

• https://www.linkedin.com/in/brittboeskov/
• https://4see.dk/4see-methods/

Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/
Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup
Join the iGaming Leader Mastermind: https://www.igamingleader.com/

In this episode of iGaming Leader, Leo sits down with Elena, a seasoned executive with extensive experience in business transformation and leadership.

Elena shares her journey from starting as a PA to leading billion-pound transformation projects in highly regulated industries.

The conversation explores navigating career transitions, the importance of leadership adaptability, and how diverse perspectives shape high-performing teams.

Elena provides actionable advice for leaders looking to progress into executive roles and lead with confidence.

Guest Bio

Elena Chambers is the Group Chief Transformation and Corporate Development Officer at Allwyn, bringing over 20 years of global experience in strategic planning and business transformation. Her journey from starting as a PA in Moscow to leading billion-pound transformations showcases her ability to drive innovation across industries.

Prior to Allwyn, she served as COO at 888holdings where she led the William Hill post-merger integration, and spent 12 years at British American Tobacco leading a £1.2bn global transformation program. A graduate of both Columbia and London Business School, Elena brings a unique perspective shaped by her cross-cultural experience, with a leadership approach that emphasizes curiosity, authenticity, and building diverse teams to drive organizational change.

Key Topics Discussed

02:00 – Elena’s career journey: From PA to leading transformation projects

03:50 – Breaking into the iGaming industry and taking on executive roles

07:20 – Managing international teams and adapting to different leadership cultures

11:50 – Leveraging strengths as a woman in a male-dominated industry

20:30 – The importance of delegation and letting go to grow as a leader

25:30 – Handling imposter syndrome and embracing continuous learning

29:00 – Lessons from the tobacco industry: Anticipating regulatory changes in gaming

32:20 – The future of national lotteries and the role of technology in transformation

Memorable Quotes

"If you try to mimic your male colleagues' behavior, that's not going to get you anywhere—be yourself and use your unique strengths."

"One of the biggest skills for a leader is to build a team that complements each other, not one that mirrors each other."

"Start transforming from the inside while you still can—don’t wait until you’re forced to change."

Important Links

Connect with Elena: https://www.linkedin.com/in/elenareznikorskaya/

Follow Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/

Subscribe to the iGaming Leader newsletter: https://www.igamingleader.com/signup

Join the iGaming Leader Mastermind: https://www.igamingleader.com/