Why "compliance" might be the worst job title in iGaming — and what it should really be called instead.

In this episode of iGaming Leader, Leo chats with Alex Henderson, VP of Compliance at Midnite and co-host of Compliance Chronicles.

From financial investigations at the UK National Crime Agency to scaling compliance teams across multiple markets, Alex reveals the hidden realities of leadership in regulated industries.

What You'll Discover:

• Why shifting from "every customer is a criminal" changes everything
• The million-dollar mistake that taught Alex his biggest leadership lesson
• How to build trust-based teams that can take calculated risks
• Real strategies for supporting teams without burning them out
• What to do when leadership decisions backfire publicly
• Why making mistakes is essential for growth (even expensive ones)

This isn't your typical compliance conversation — it's raw, practical leadership advice for anyone managing teams in complex, regulated environments.

🎧 IN THIS EPISODE

00:00 – Why "compliance" is the worst possible name for the role
04:00 – Shifting mindset: not every customer is a criminal
07:00 – Leadership by trust: enabling teams to take risks
10:00 – When quick decisions backfire and cost millions
14:00 – Customer experience in gambling: speed dating or lost forever
15:00 – Building a compliance team from 1 to 30+ people
17:00 – Hard leadership lessons: overwork, burnout, and compassion
28:00 – Losing respect publicly and how to recover trust
36:00 – When things go wrong and you're blamed unfairly
40:00 – Handling redundancies and supporting people afterwards
44:00 – What makes a "great leader" and the role of mistakes

💡 KEY QUOTES FROM THIS EPISODE

"The whole role of working in compliance is protection."

"I'd rather go full-flat being innovative than follow mediocracy."

"I cost the company a lot of money there… fantastic for compliance, but commercially a massive impact."

"I was told early on: don't build relationships with your team because you'll have to fire them. I learned the hard way that's exactly what you should do."

"I'll never stop making mistakes. They're the biggest lessons I've had in leadership."

🔗 CONNECT & FOLLOW

• Alex Henderson on LinkedIn: https://www.linkedin.com/in/alexanda-h-114911145/
• Leo Judkins on LinkedIn: https://www.linkedin.com/in/leo-judkins/
• Subscribe to iGaming Leader newsletter: https://www.igamingleader.com/signup
• Join the iGaming Leader Mastermind: https://www.igamingleader.com/
  
  

ABOUT THE GUEST Alex Henderson brings extensive experience in compliance, regulatory affairs, and operational risk within the gambling sector. His career spans work with leading operators, law enforcement agencies, and advisory firms, giving him a unique perspective on both commercial and regulatory challenges. He co-hosts The Compliance Chronicles, a podcast helping peers navigate complex regulatory environments.

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