From Dial-Up to Digital Transformation: Three Decades of Technology Evolution

The technology landscape has changed dramatically since 1995, when dial-up modems were the gateway to digital communication and online communities. Over nearly three decades, I’ve had the opportunity to work across many facets of this evolution, starting with tech support at an early internet service provider and progressing through systems administration, network engineering, and network administration roles. These experiences provided insights into how organizations build and maintain their digital infrastructure, from running networks at large hosting companies to contributing to early content delivery network (CDN) development during the internet’s rapid expansion.

The corporate world offered different perspectives on technology challenges. At Cisco, my roles included working as a core routing and switching sales engineer supporting major enterprise clients, and later as a theater consulting systems architect focused on emerging markets. This work involved contributing to the SEVT program and supporting Cisco Live events in developing regions, which highlighted how technology needs vary dramatically across different markets and organizational contexts. Later experience with value-added resellers provided exposure to diverse network implementations across industries including streaming media, data centers, sports organizations, financial services, legal firms, and energy companies. Each sector brought unique requirements, constraints, and success metrics that shaped my understanding of how technology serves organizational goals. Returning to consulting in mid-2024 created an opportunity to synthesize these varied experiences into a focused approach to organizational problem-solving.

What became clear throughout this journey is that organizations often struggle with complex, interconnected challenges that don’t have straightforward technical solutions. These “wicked problems” require understanding tradeoffs, considering multiple perspectives, and applying systems thinking to see how different parts of an organization interact and influence each other. While technology is often part of the solution, many organizational challenges stem from communication gaps, misaligned incentives, unclear processes, or competing priorities rather than purely technical limitations.

This experience revealed that organizations frequently add complexity when simplicity would be more effective. This tendency to overcomplicate solutions often stems from wanting to address every possible scenario upfront, rather than building adaptable systems that can evolve. There’s real value in finding elegant, straightforward approaches that solve core problems while remaining flexible enough to accommodate change. This philosophy extends beyond individual solutions to organizational transformation itself—helping companies identify what really matters, eliminate unnecessary complexity, and build capabilities that support their actual goals rather than theoretical requirements.

Solvesight emerged from this recognition that organizations benefit most from advisors who can see across domains, understand how different organizational systems interact, and help simplify complex challenges into manageable solutions. Rather than focusing solely on technical implementation, we emphasize understanding what organizations are trying to achieve, identifying the real constraints they face, and developing practical paths forward that account for both technical and human factors.