The average enterprise uses 44% of the Microsoft stack it's paying for.
Denis O'Shea measured it: the same 120 point assessment, run across hundreds of organizations, and the number doesn't move. The other 56% sits licensed and idle while the same teams buy third party tools to cover gaps Microsoft 365 already covers.
Denis is the founder of Mobile Mentor and has managed 14.5 million enterprise devices across healthcare and financial services. He has seen the sprawl from the inside: security tools purchased because insurance required them, then never properly deployed.
In this episode, Max and Denis cover the utilization problem, what going passwordless actually requires when legacy apps resist it, what the Digital Markets Act changed in your mobile attack surface, and why the best security is the kind employees never notice.
If you're signing off on a Microsoft renewal in the next 90 days, or your security stack has grown every year without your confidence growing with it, this is the episode.
What You'll Learn
- How much of your Microsoft stack you're actually using, and where the rest went
- What changed in your mobile attack surface the day the Digital Markets Act took effect
- Why mobile threat defense moved from optional to required
- How to justify security spend with no obvious ROI to a board that doesn't want to hear it
- What's replacing MDM as the market consolidates
- Why deploying Intune yourself usually costs more than paying someone else to do it
In this conversation:
- (00:00) - Cold open: the average enterprise is using 44% of what it bought
- (01:07) - Intro: Mobile Mentor, and the question that isn't as soft as it sounds
- (01:32) - Origin story: the Nokia deal lost to Orange, and why that changed everything
- (05:16) - Why Blackberry won on ease of use, and what that unlocked in the enterprise
- (07:02) - The 2008 crash, and the pivot from one-on-one service to managed mobile provider
- (08:19) - The double edged sword: consumer tech experience raising enterprise expectations
- (09:45) - BYOD vs. corporate-owned: where companies actually get into trouble
- (13:32) - The middle ground: manage the data and apps, never the personal device
- (15:21) - Exfiltration vs. infection, and why some companies lock down tight while others ratchet up after bad things happen
- (17:17) - The infinity loop: security vs. employee experience, and 92 apps updating a day
- (19:28) - Is a BYOD stipend a bad idea
- (20:18) - What the Digital Markets Act broke in your mobile security model
- (23:07) - Why mobile threat defense is now a requirement, not an option
- (26:03) - The ROI problem: how to justify security spend that has no obvious return
- (30:43) - Executive smishing, and why phone impersonation is catching up to email
- (32:27) - AI in the wrong hands: what unmanaged devices look like in 2026
- (37:33) - Is there still room for third-party vendors once Microsoft dominates the stack
- (39:49) - Why the MDM market is disappearing — and what replaces it
- (45:53) - 52 security tools, mostly siloed: how enterprises accumulated the wrong defenses
- (49:44) - You're using 44% of your Microsoft stack — and buying tools to cover the rest
- (52:06) - What actually triggers a company to go looking for help
- (55:18) - The manual IT problem: two hours per device, every device, still happening
- (56:47) - Why Europe wants to unbundle, and why Microsoft just re-bundled harder with E7
- (01:00:25) - The pricing illusion: a $100 bundle hiding a dozen billion-dollar products
- (01:02:22) - Why the business is about people, not the tech stack underneath it
- (01:04:36) - The DIY trap: why deploying Intune yourself costs more than you think
- (01:06:57) - 400,000 Microsoft partners, and how to actually find the right one
- (01:09:48) - The ServiceNow lesson: DIY versus a partner who's done it before
- (01:10:21) - The real maturity signal: has the company moved to enterprise suite licensing
- (01:12:47) - Three things to remove from your IT team's plate this year
- (01:14:26) - Why going passwordless is a board decision, not an IT project
- (01:15:59) - How to explain passwordless to a non-technical leader without acronyms
- (01:21:11) - AI-enabled attacks and why your on-prem infrastructure can't keep up
- (01:23:04) - Set your own end-of-life date before Microsoft sets it for you
- (01:23:44) - Why "protect users, devices, network" isn't the whole model anymore
- (01:25:09) - Data as the new frontier: why Purview and classification matter more than ever
- (01:26:42) - How to sell security investment to a board that doesn't want to hear about it
- (01:27:48) - Invisible security: what good looks like when it's working
- (01:31:11) - Closing: the lens is always the end user's day
What We Mentioned:
Mobile Mentor
Microsoft Intune
Microsoft Entra / Entra Suite
Microsoft Defender
Microsoft Sentinel
Microsoft Purview
Microsoft 365 (E3, E5, E7)
Microsoft Agent 365
Windows Autopilot
Active Directory (AD)
SCCM (System Center Configuration Manager)
Jamf
SOTI
Omnissa Workspace ONE (formerly AirWatch)
Lookout
Zimperium
Wandera (now part of Jamf), referenced in the episode as "Wander"
Digital Markets Act (DMA)
BYOD (Bring Your Own Device)
COPE (Corporate Owned, Personally Enabled)
MDM / UEM / MTD (Mobile Device Management / Unified Endpoint Management / Mobile Threat Defense)
EDR (Endpoint Detection and Response)
Zero touch provisioning
Hot patching (Windows updates without restart)
ServiceNow
Windows 10 end of life (October 14, 2025)
About Denis O'Shea
Denis O'Shea is the founder and CEO of Mobile Mentor, a Microsoft specialized managed services provider that has enabled 14.5 million devices across enterprise clients in healthcare, financial services, and beyond. He spent 15 years at Nokia running operations across seven countries before building a company around a problem he kept seeing: organizations paying for technology they couldn't fully use. He has served on Microsoft's Intune product advisory board and has spent the last decade helping enterprises close the gap between what they bought and what's actuall...
