Navigating the Windows 11 Shift: Strategic Insights for IT Leaders

Aug 28, 2025 12:00 PM1:00 PM EDT

Request The Full Recording

Here's what we talked about

  • Assessing current device fleet readiness
    • Learn how IT leaders are using readiness data to prioritize upgrades and avoid bottlenecks during rollout.
  • Addressing the end-of-support risks for Windows 10
    • Explore mitigation strategies that maintain protection while phasing in Windows 11 adoption.
  • Identifying upgrade paths vs. replacement needs
    • Learn how to determine which devices can be upgraded cost-effectively and which require replacement to meet Windows 11 requirements.
    • See how aligning hardware refresh cycles with OS migration can optimize budgets and minimize disruption.
  • Aligning OS transition with broader digital transformation goals
    • Discover how leading enterprises are integrating Windows 11 migration into long-term modernization roadmaps and security initiatives.

Event Partners

Microsoft Windows

Microsoft is the largest vendor of computer software in the world. It is also a leading provider of cloud computing services, video games, computer and gaming hardware, search and other online services. Microsoft's corporate headquarters is located in Redmond, Wash., and it has offices in more than 60 countries.

Intel

Intel Corporation is a global leader in semiconductor manufacturing and technology solutions. Intel designs and produces advanced microprocessors, integrated graphics, chipsets, and other computing components that power a wide range of devices, from personal computers and data centers to networking, artificial intelligence, and edge computing systems.

Insight Enterprises

Insight Enterprises, Inc. is a Fortune 500 solutions integrator helping organizations accelerate their digital journey to modernize their business and maximize the value of technology. Insight’s technical expertise spans cloud and edge-based transformation solutions, with global scale and optimization built on 33+ years of deep partnerships with the world’s leading and emerging technology providers.

Guest Speakers

BWG Connect

Enterprise IT Subject Matter Expert

Our moderator brings decades of experience leading infrastructure, cloud transformation, and enterprise technology strategy across finance, media, publishing, and healthcare sectors. They have overseen IT infrastructure, large-scale digital transformation, and DevOps initiatives for some of the world’s most complex enterprise organizations, bridging strategy and execution to deliver measurable business impact. Their deep expertise ensures every discussion is grounded in real-world insight and informed by a career at the forefront of technological change.

Joe Flynn LinkedIn

Director of Services at Insight

With over 25 years of experience in the IT industry, Joe loves that technology constantly changes and provides new challenges, pushing him to learn more every day. As a leader for a vendor-agnostic organization, Joe is equipped to advise clients on the solutions that drive the best value for their business. He is a champion across many technologies and approaches knowledge-sharing not as a one-time project but as a continued mindset.

Rob McGilvrey LinkedIn

Americas Specialist | Windows Commercial Device Partner Sales at Microsoft

Rob McGilvrey is a seasoned technology sales leader with over 15 years of experience across the commercial, education, government, and healthcare sectors. Currently serving as an Americas Specialist at Microsoft, he focuses on modern endpoint solutions, including Windows 11 Pro, Microsoft 365, Microsoft Intune, and Windows Autopilot. Rob is recognized for his strategic insights into digital transformation and his ability to drive impactful conversations around AI integration, endpoint security, and hybrid work enablement. Rob brings both technical expertise and a collaborative approach to helping organizations modernize their IT environments.

Event Moderator

BWG Connect

Enterprise IT Subject Matter Expert

Our moderator brings decades of experience leading infrastructure, cloud transformation, and enterprise technology strategy across finance, media, publishing, and healthcare sectors. They have overseen IT infrastructure, large-scale digital transformation, and DevOps initiatives for some of the world’s most complex enterprise organizations, bridging strategy and execution to deliver measurable business impact. Their deep expertise ensures every discussion is grounded in real-world insight and informed by a career at the forefront of technological change.

Joe Flynn LinkedIn

Director of Services at Insight

With over 25 years of experience in the IT industry, Joe loves that technology constantly changes and provides new challenges, pushing him to learn more every day. As a leader for a vendor-agnostic organization, Joe is equipped to advise clients on the solutions that drive the best value for their business. He is a champion across many technologies and approaches knowledge-sharing not as a one-time project but as a continued mindset.

Rob McGilvrey LinkedIn

Americas Specialist | Windows Commercial Device Partner Sales at Microsoft

Rob McGilvrey is a seasoned technology sales leader with over 15 years of experience across the commercial, education, government, and healthcare sectors. Currently serving as an Americas Specialist at Microsoft, he focuses on modern endpoint solutions, including Windows 11 Pro, Microsoft 365, Microsoft Intune, and Windows Autopilot. Rob is recognized for his strategic insights into digital transformation and his ability to drive impactful conversations around AI integration, endpoint security, and hybrid work enablement. Rob brings both technical expertise and a collaborative approach to helping organizations modernize their IT environments.

Request the Full Recording

Please enter your information to request a copy of the post-event written summary or recording!

How can we help?

Hang tight! An event summary, key takeaways, & a full transcript will be posted shortly. In the meantime... How can we help?

What is BWG Connect?

BWG Connect provides executive strategy & networking sessions that help brands from any industry with their overall business planning and execution. BWG has built an exclusive network of 125,000+ senior professionals and hosts over 2,000 virtual and in-person networking events on an annual basis.
envelopephone-handsetcrossmenu linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram