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

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 IT Connect with Corey:  * https://www.linkedin.com/in/corey-wisdom-553a1611/ [https://www.linkedin.com/in/corey-wisdom-553a1611/] * https://www.linkedin.com/company/rl-canning/ [https://www.linkedin.com/company/rl-canning/] * https://app.technologymatch.com/solutions/servicenow [https://app.technologymatch.com/solutions/servicenow]

Everyone’s Talking About AI, But No One’s Saying This with Raheela Nanji

AI is moving fast, but most leaders aren’t talking enough about the human side of what this moment is actually creating inside organizations: fear, uncertainty, imposter syndrome, and the pressure to adapt in real time.  In this conversation, Tonya sits down with leadership coach and business strategist Raheela Nanji to unpack what leadership really looks like in the AI era and why the biggest challenge organizations face right now isn’t the technology itself. It’s how leaders guide people through the uncertainty surrounding it. Drawing on more than 25 years of experience across technology, marketing, and business leadership, Raheela shares what she’s seeing behind the scenes inside organizations navigating AI adoption, from confusion and panic to innovation and possibility. Together, they explore why psychological safety, empathy, curiosity, and communication are becoming the most important leadership skills in modern business.  In this episode, they explore: *  Why AI is reshaping jobs rather than simply replacing them  *  The hidden fear, uncertainty, and imposter syndrome leaders aren’t openly discussing  *  Why psychological safety matters more than ever inside organizations  *  How leaders can communicate AI initiatives without creating panic or resistance  *  The danger of relying on AI without critical thinking and human oversight  *  Why curiosity and empathy are becoming essential leadership skills in the AI era  *  What organizations are getting wrong with AI spending and strategy  *  How companies are using AI to scale knowledge, systems, and decision-making  *  Why vulnerability and transparency build stronger leadership trust during uncertainty  *  How AI is exposing leadership gaps that already existed beneath the surface  *  The importance of helping teams adapt instead of pretending leaders have all the answers  *  What separates organizations that will successfully evolve with AI from those that fall behind Connect with Raheela: https://www.linkedin.com/in/raheelananji/ [https://www.linkedin.com/in/raheelananji/] https://ree-consulting.com/ [https://ree-consulting.com/]

AI Is Exposing Security Gaps Most Companies Don’t See: Why Reactive Security is Failing And What IT Leaders Need To Do Next with John Fraser

AI is accelerating cybersecurity threats faster than most organizations are prepared for, and this episode will challenge the way you think about security, visibility, and prevention in the age of AI. In this conversation, Tonya sits down with cybersecurity strategist John Fraser to unpack how AI is exposing security gaps inside organizations and why traditional “detect and respond” models are no longer enough. With experience spanning Department of Defense programs, enterprise IT environments, and high growth SaaS ecosystems, John brings a practical perspective on what’s actually happening inside modern security teams and where companies are falling behind. In this episode, they explore: *  Why AI is exposing security gaps most organizations don’t even realize they have  *  How rogue AI usage inside companies is creating massive risk  *  What happens when employees upload company data into LLMs and AI tools  *  Why “detect and respond” security models are struggling to keep up  *  How ransomware attacks have accelerated from days to minutes  *  The real reason security teams are overwhelmed with alerts  *  How AI is lowering the barrier to entry for cybercrime  *  Why attackers are using AI to scale malware and phishing attacks  *  The hidden risks of AI coding tools and copilots  *  Where traditional zero trust security approaches fall short  *  Why VPNs create dangerous visibility blind spots  *  What organizations are missing when it comes to cloud security visibility  *  The difference between reactive security and preemptive threat prevention  *  Why visibility into network traffic matters more than ever  *  What modern inline threat prevention looks like in practice  *  How organizations can reduce alert fatigue and SOC overload  *  Why companies need to treat AI as both a productivity tool and a security threat  *  What separates organizations that adapt from those that fall behind in the AI era  Connect with John: John.fraser@trinitycyber.com

Your Employees Already Work From Anywhere, Your Infrastructure Doesn’t with Jess Jorgensen

If flexible work feels like the future but your infrastructure still feels stuck in the past, this episode is going to challenge how you think about connectivity, security, and control. In this conversation, Tonya sits down with Jess Jorgensen, founder and CEO of Go Roam Tech and Blush Technology Group, to unpack what’s really happening as work becomes untethered from place. From RVs and remote canyons to enterprise environments, Jess shares what breaks when people move faster than infrastructure and why most organizations are still operating on systems that were never designed for this reality. They dive into the hidden risks of distributed work, the growing gap between IT responsibility and control, and what it actually takes to support a workforce that can log in from anywhere. Jess brings a rare, real world perspective from living and working fully remote, showing how the same foundational principles apply whether you’re running an enterprise network or working from the road. This episode is a practical and eye opening look at what it means to build infrastructure that moves with your business and why the future of IT starts at the edge.   In this episode, they explore: * Why flexible work is already happening with or without company approval * Where infrastructure actually breaks in remote and hybrid environments * The hidden risks of patchwork systems built during COVID * Why one internet connection is effectively zero in a remote world * How security gaps are expanding as employees work from uncontrolled environments * What IT leaders are underestimating when it comes to AI and remote access * Why shadow IT and unauthorized tools are accelerating risk * The real reason remote work is now a talent acquisition and retention strategy * How poor user experience drives employees to create risky workarounds * What it takes to create secure, always on connectivity anywhere * Why IT must shift from control to enablement in a decentralized world * How to rethink your tech stack for the next 12 to 18 months   Important Links: https://app.technologymatch.com/solutions/working-from-roam [https://app.technologymatch.com/solutions/working-from-roam] https://app.technologymatch.com/solutions/advisory-services-1 [https://app.technologymatch.com/solutions/advisory-services-1]

What IT Leaders Still Get Wrong About Data in the AI Era with NetApp’s Ray LaMarca

If AI feels like the right move but you’re still not seeing results, this episode reframes where the real problem is. In this conversation, Tonya sits down with Ray LaMarca, Director of Solutions Engineering at NetApp, to unpack why most AI initiatives stall out before they ever deliver value. It’s not the tools. It’s the foundation underneath them. They break down what’s actually going wrong behind the scenes, from siloed data and security risks to misalignment between business and IT. Ray shares what he’s seeing across enterprise teams, where companies are overspending, and why ROI is taking longer than expected. This episode is a grounded look at what it really takes to turn AI from an experiment into a strategic advantage and why it all starts with your data.   In this episode, they explore: * Why most AI projects fail before they ever reach production and what’s really causing it * The hidden breakdown between business and IT and how it impacts results * Why data security is still the number one concern for IT leaders in the AI era * How siloed data systems create inefficiencies, risk, and missed opportunities * What actually happens when your data isn’t clean, complete, or protected * Why massive investments in GPUs and cloud infrastructure aren’t delivering ROI * The real reason companies are slow to see value from AI initiatives * How supply chain, timing, and misaligned investments derail outcomes * Why asking better questions is the fastest way to avoid failure * What it means for IT to shift from cost center to revenue driver * How partnerships, not just products, determine success in modern IT strategy * Real world examples of companies using AI and data to drive efficiency and innovation * What IT leaders should prioritize over the next 12 to 18 months to stay competitive   Important Links: https://app.technologymatch.com/solutions/netapp-ai-data-engine [https://app.technologymatch.com/solutions/netapp-ai-data-engine] https://app.technologymatch.com/solutions/netapp-afx [https://app.technologymatch.com/solutions/netapp-afx]