From Legacy to Legendary: Tackling Tech Debt for AI Readiness
Dec 4, 2025 6:00 PM - 8:30 PM EDT
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 Outdated infrastructure, siloed systems, and inflexible architectures can slow innovation, increase risk, and drain resources needed for transformation.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 dinner 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 us for an interactive discussion over drinks and dinner with your peers! We'll explore the latest trends in the space and get your questions answered.
As always, there will be no sales pitches and dinner is complimentary.
Seating is limited, and RSVP is required.
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.
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.
Solutions Director for Compute & AI at Insight
A distinguished Principal Architect at Insight with over 20 years of experience in IT specializing in data-center technologies, Dean excels in leading senior architect and engineering teams for complex projects. His expertise extends to cross-functional collaboration, evident in his strategic partnerships with global teams, driving cross-sell opportunities and significant business growth. Dean's ability to convey complex concepts effectively has been honed through his dedication to understanding client businesses and market dynamics, ensuring alignment with client strategies for optimal outcomes. His proficiency spans various technologies, including Cisco converged architectures, Nutanix hyperconverged solutions, data storage from Pure Storage and NetApp, and VMware products. Currently, he is engaged in designing private and hybrid cloud architectures to meet clients' evolving needs.
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.
Solutions Director for Compute & AI at Insight
A distinguished Principal Architect at Insight with over 20 years of experience in IT specializing in data-center technologies, Dean excels in leading senior architect and engineering teams for complex projects. His expertise extends to cross-functional collaboration, evident in his strategic partnerships with global teams, driving cross-sell opportunities and significant business growth. Dean's ability to convey complex concepts effectively has been honed through his dedication to understanding client businesses and market dynamics, ensuring alignment with client strategies for optimal outcomes. His proficiency spans various technologies, including Cisco converged architectures, Nutanix hyperconverged solutions, data storage from Pure Storage and NetApp, and VMware products. Currently, he is engaged in designing private and hybrid cloud architectures to meet clients' evolving needs.
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.
