You Bought the Stack. You're Using Half of It.

You Bought the Stack. You're Using Half of It.

From Tech Deep Dive by ITBroker.com

June 2, 2026 · 1h 33m · Episode 209

About this episode

Denis O'Shea discusses the underutilization of the Microsoft stack in enterprises and the challenges of achieving passwordless security.

The average enterprise uses 44% of the Microsoft stack they're paying for. Denis O'Shea knows because he's measured it — the same 120-point assessment, hundreds of organizations, the number doesn't move. The other 56% is licensed and sitting idle while the same teams buy third-party tools to fill gaps that 365 already covers. Denis is the founder of Mobile Mentor and has managed 14.5 million enterprise devices across healthcare and financial services. He's seen what the stack looks like from the inside — the sprawl, the overlap, the security tools that got purchased because insurance required it. Never properly deployed. In this episode, Max and Denis work through the utilization problem, what it actually takes to go passwordless when your legacy apps will fight you, what the Digital Markets Act opened up in your mobile attack surface, and why the best security your employees will ever experience is the kind they never notice. If you're signing off on a Microsoft renewal in the next 90 days, or your security stack has grown every year and your confidence in it hasn't — this is the episode. Find your situation. Skip to the answer. We've been trying to go passwordless for two years…

People in this episode

Host: Max

Guest: Denis O'Shea

Topics covered

  • Microsoft stack utilization
  • enterprise technology
  • security tools
  • passwordless authentication
  • Digital Markets Act
  • IT management

Keywords

  • Microsoft stack
  • enterprise devices
  • security tools
  • passwordless
  • Digital Markets Act
  • IT maintenance
  • third-party tools

Mentioned in this episode

Organizations: Mobile Mentor, Microsoft, ITBroker.com

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