Where AI Ambition Meets the Endpoint Budget

Sep 16, 2026 1:00 PM2:00 PM EST

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Event Description

The pressure to make the workforce AI-ready has collided with the pressure to justify every dollar of hardware spend. IT leaders are being asked to modernize endpoints for AI and tighten security at the same moment budget scrutiny is sharpest, and the two mandates rarely point in the same direction. The case for new devices pulls toward investment while finance review and fleet complexity pull the other way, leaving leaders to decide what genuinely warrants the spend and what is vendor momentum dressed as necessity.

This session brings together infrastructure and end-user-compute leaders to compare how they are making that call. The conversation looks at which AI use cases actually require modern hardware like Copilot+ PCs, how the security case for Windows 11 Pro holds up against an aging mixed fleet, and how to build a refresh case that survives finance review rather than defaulting to a vendor's replacement timeline. With Insight and Microsoft contributing a practitioner's view, it also examines where device modernization actually closes the gap for the workforce and where consolidation simplifies operations versus quietly shifting complexity elsewhere.

Attendees leave with sharper ways to separate necessary investment from vendor pressure, frame endpoint spend in terms their finance partners accept, and prioritize the modernization moves that return the most for the budget they have.

BWG Connect, Insight Enterprises & Microsoft Windows invite you to join an interactive event with industry peers to review & discuss practical insights across the digital space.

As always, there will be no sales pitch and all attendees are welcome to listen and learn.

Discussion Topics

  • Turning AI strategy into business outcomes
    • Separating the AI workloads that need new hardware from the ones that don't, before committing budget to a refresh.
  • Modern endpoint security for today's cyber threats
    • Weighing the exposure of extending older endpoints another cycle against the price of modernizing them now.
  • Maximizing ROI from device refresh investments
    • Deciding what genuinely warrants the spend versus what's vendor momentum dressed as necessity.
  • Future-ready workforce experiences powered by Windows
    • Closing the gap between the employee experience leaders are expected to deliver and the fleet and budget they have to work with.
  • Reducing IT complexity while improving user productivity
    • Where consolidation genuinely simplifies operations versus where it just shifts the complexity somewhere else.

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.

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.

Matt Spero LinkedIn

Business Development Manager, Windows Pro at Insight Enterprises

Matt works as an Business Development Manager for Windows Pro at Insight where he serves as a trusted advisor to partners while assisting in formulating strategy and direction for business needs relating to Microsoft & Insight devices and services.

Kirk Sinclair LinkedIn

Channel Account Manager at Microsoft Windows

Experienced Sales Executive with a demonstrated history of working in the IT Channel. Strong sales professional skilled in Partner Relationship Management, Go-to-market Strategy, Channel Management, Pricing Strategy, and both Commercial and Consumer Electronics.

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.

Matt Spero LinkedIn

Business Development Manager, Windows Pro at Insight Enterprises

Matt works as an Business Development Manager for Windows Pro at Insight where he serves as a trusted advisor to partners while assisting in formulating strategy and direction for business needs relating to Microsoft & Insight devices and services.

Kirk Sinclair LinkedIn

Channel Account Manager at Microsoft Windows

Experienced Sales Executive with a demonstrated history of working in the IT Channel. Strong sales professional skilled in Partner Relationship Management, Go-to-market Strategy, Channel Management, Pricing Strategy, and both Commercial and Consumer Electronics.

Interested in joining? Request an invitation below.

Please provide the information and we will be in touch!

Need help with something else?

Aaron Conant

Co-Founder & Managing Director at BWG Connect


BWG Connect provides executive strategy & networking sessions that help brands from any industry with their overall business planning and execution.

Co-Founder & Managing Director Aaron Conant runs the group & connects with dozens of brand executives every week, always for free.


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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.
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