Microsoft 365 Copilot Readiness Is both a Security & Licensing Problem

Tony Mackelworth, CEO and founder of Softspend, has spent over a decade in the Microsoft licensing ecosystem — and his view on AI readiness cuts against the market consensus. Most organisations are treating Copilot readiness as a procurement exercise. Tony argues it's a security posture problem first. If your identity, configuration, and compliance foundations are broken before you switch Copilot on, you've just given it the flawed risk posture of every user it's attached to. In this episode we cover: Why Copilot readiness assessments should start with Defender, Purview, and Entra — not license counts How Zero Trust and CIS frameworks apply to M365 security posture today The agent governance gap: visibility, cost allocation, and ownership at scale Joiners, movers, leavers — but now for your agent fleet Why the spreadsheet can't survive the agent ecosystem Microsoft's shift from ARPU to ARPA — and what a per-agent licensing model means for SAM and FinOps practitioners Governance technical debt: what happens when Copilot gets sold and nobody owns the security foundations If you're working in ITAM, SAM, or FinOps and advising clients on Microsoft 365, this is the commercial and governance context you need before that next conversation. 🎙️ Guest: Tony Mackelworth, CEO & Founder, Softspend 🎙️ Host: Shaun Ashbury 📺 Off Menu IT — sponsored by Licenseware 🔗 Connect with Tony:   / tonymackelworth   🔗 Softspend: https://softspend.com/ 🔗 Softspend on LinkedIn:   / softspend   🔗 Licenseware: https://licenseware.io