The Cheapest Decision in IT Is the Most Expensive One: Why Mid-Market Tooling Choices Are Quietly Capping Your AI Strategy with Corey Wisdon

What if the technology decision that saved your company money three years ago is the very thing slowing your growth today?In this season two finale of Between Fires and Futures, Tonya sits with Corey Wisdon to unpack one of the biggest hidden problems in mid-market IT: the long-term cost of “cheap and fast” infrastructure decisions.Corey shares the story of a $3 million enterprise deployment that took eight months before users could even log in, and how that experience completely changed the way he approaches IT strategy, ServiceNow implementations, and AI adoption today. They also dive into the surprising reality behind enterprise deployments, the burnout happening on service desks, and why simplicity, integration, and long-term thinking matter more than ever in 2026.Tune in to hear: Why the “fast and cheap” IT decision often becomes the most expensive one later  The hidden costs of fragmented tool stacks and over-customized platforms  What really causes enterprise deployments to stall after go-live  Why many organizations are failing to see ROI from AI tools  The biggest mistakes companies make when rolling out AI internally  How poor governance creates “agent sprawl” inside organizations  Why mid-market companies are underserved by enterprise IT vendors  The difference between ticketing systems and scalable enterprise platforms  How RL Canning’s hosted ServiceNow model gets organizations live in just 45 days  The importance of roadmap thinking instead of reactive technology purchases  Why simplicity is becoming the most important strategy in modern ITConnect with Corey: https://www.linkedin.com/in/corey-wisdom-553a1611/https://www.linkedin.com/company/rl-canning/https://app.technologymatch.com/solutions/servicenow