From Legacy to Legendary: Tackling Tech Debt for AI Readiness

Nov 11, 2025 3:00 PM4:00 PM EST

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Event Description

AI is no longer experimental at the enterprise level, it is a core driver of competitive advantage. But without the right foundation, even the most ambitious AI initiatives can stall before they begin. For many organizations, the primary barrier is technical debt. Outdated infrastructure, siloed systems, and inflexible architectures can slow innovation, increase risk, and drain resources needed for transformation.

This session is designed for senior IT leaders who must modernize at scale without disrupting critical operations. We will explore how to quantify the cost of technical debt, free up resources for AI workloads, and create a future-ready infrastructure that supports scalable AI adoption. You’ll leave with a practical framework for prioritizing modernization projects, building alignment with the business, and delivering measurable ROI.

BWG Connect & Insight Enterprises 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

  • Understanding the True Cost of Tech Debt
    • Learn how to identify and measure the operational, financial, and innovation costs tied to aging systems and accumulated technical debt.
    • Discuss how unchecked tech debt limits agility, increases risk, and directly impacts the success of AI initiatives.
  • Modernization Without Disruption
    • Explore strategies for upgrading infrastructure and applications without compromising uptime or service levels.
    • Hear how enterprise teams are sequencing modernization projects to deliver value early while avoiding transformation fatigue.
  • Releasing Legacy Resources for AI Workloads
    • How to free compute, storage, and networking capacity from outdated workloads to power AI-driven applications.
    • Learn how targeted decommissioning and workload migration can unlock performance gains and cost savings.
  • Building Future-Ready Infrastructure
    • Discover how to design enterprise architectures that can scale with evolving AI models, data demands, and compliance requirements.
    • How integrating cloud, edge, and on-prem resources creates a flexible, resilient foundation for AI.
  • Where to Start: Assessments, Strategy, and ROI
    • Learn how to conduct an accurate readiness assessment to prioritize modernization efforts based on AI business goals.
    • Explore how to create a compelling ROI narrative that secures budget and cross-functional buy-in for transformation.

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.

Guest Speaker

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.

Jeff Bozic LinkedIn

Principal Architect and Distinguished Technologist at Insight Enterprises

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.

Jeff Bozic LinkedIn

Principal Architect and Distinguished Technologist at Insight Enterprises

Interested in joining? Request an invitation below.

Please provide the information and we will be in touch!

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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