Casey Lindsay

Casey Lindsay is a Strategic Software Consultant with Connection’s XLO Practice. Casey brings over 15 years of vast Microsoft experience helping Connections’ clients navigate all the complex decisions surrounding their Microsoft technology and investment strategies. When not tackling Microsoft decisions, Casey can be found outside spending time with his family traveling with their RV to create lasting memories doing things like hiking, kayaking, and paddleboarding.

Microsoft 365 E7 – The Frontier Worker Suite: The Intersection of Security, Compliance, and AI

March 19, 2026 | Casey Lindsay

Ever since the dawn of Copilot (circa early 2023), our customers have been asking about the possibility of Microsoft bundling Copilot with M365 E5. It was merely conjecture during those…

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The Evolution of the Microsoft Partner Ecosystem

May 22, 2025 | Casey Lindsay

With the dust settling from the recent celebration of Microsoft’s 50th birthday in April, I thought it would be timely to sit down and put my thoughts on paper. Having worked…

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Is Software Asset Management Still Relevant? Our Answer May Surprise You

August 6, 2024 | Casey Lindsay

My career has had me closely intertwined with Software Asset Management (SAM) and IT Asset Management (ITAM) since 2006. Over this stretch of 18 years, I have helped to pioneer…

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Microsoft’s Teams Unbundling: What’s the Impact on Your Organization?

May 2, 2024 | Casey Lindsay

It’s that time of the year again…spring has sprung, the flowers are in full bloom, the grass is growing fast, it’s such a rebirth of life—and with that comes another…

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ChatGPT, AI, and Machine Learning—Oh My!

June 8, 2023 | Casey Lindsay

I often wonder to myself, at what point does AI, ChatGPT, Machine Learning—and frankly just trying to stay at the bleeding edge of the technological revolution—get to the point of…

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