The Cost of Waiting on Device Modernization

Jan 12, 2026 3:00 PM4:00 PM EDT

Register

Event Description

Device modernization has quietly become a timing decision. As Windows 10 reaches end of support, security risks increase, productivity expectations rise, and AI-capable hardware enters the mix, many organizations are finding that waiting feels safer than acting, even as the costs continue to accumulate.

This peer-driven discussion brings together IT and business leaders to compare how they are navigating device decisions today, where delays have already created friction or exposure, and how they are determining when waiting is no longer the lowest-risk option.

BWG Connect, Insight Enterprises & Dell Technologies 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

  • Many organizations are delaying device modernization because the decision feels complex and disruptive, even as the hidden costs quietly compound.
    • Attendees will compare where waiting has created friction across security, employee experience, and IT operations, including environments still running Windows 10.
  • Windows 10 end of support is turning device strategy into a timing decision rather than a technical preference.
    • Peers will discuss how they are weighing migration risk, internal readiness, and budget constraints tied specifically to Windows 11 adoption.
    • The conversation will surface where delaying upgrades limited access to newer security and management capabilities available on modern Dell devices.
  • Productivity expectations continue to rise while employee devices struggle to keep pace with how work is actually getting done.
    • Attendees will compare where outdated hardware is slowing workflows in subtle but measurable ways.
    • The group will discuss how leaders are validating real productivity gains versus assumed benefits.
  • Endpoint security is becoming harder to manage as hybrid work expands the attack surface and devices age.
    • The discussion will explore how hardware-level security is changing endpoint risk conversations.
    • Peers will share where older devices have limited their ability to respond to new threats.
  • Device refresh cycles are now being scrutinized as financial decisions, not routine IT upgrades.
    • Finance and IT leaders will compare how they are building ROI cases that extend beyond specs and benchmarks.
    • The group will discuss cost signals that indicated waiting was no longer the cheaper option.

Event Partners

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.

Dell Technologies

Dell Technologies Inc is a provider of desktop personal computers, software, and peripherals. The company designs, develops, manufactures, markets, sells, and supports information technology infrastructure such as laptops, desktops, mobiles, workstations, storage devices, software, cloud solutions and notebooks.

Guest Speakers

Anna Donnelly LinkedIn

Services Product Manager at Insight Enterprises

Specializing in communications and collaboration technology with more than 10 years of experience in the Microsoft space, Anna strives to help organizations understand how modern workplace technology can positively impact their businesses and employees.

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.

Chip Boyd LinkedIn

Channel CSG Field Product Marketing Lead, Dell Global Marketing

Event Moderator

Anna Donnelly LinkedIn

Services Product Manager at Insight Enterprises

Specializing in communications and collaboration technology with more than 10 years of experience in the Microsoft space, Anna strives to help organizations understand how modern workplace technology can positively impact their businesses and employees.

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.

Chip Boyd LinkedIn

Channel CSG Field Product Marketing Lead, Dell Global Marketing

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.


Schedule a free consultation call

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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