Between Fires and Futures: Real Conversations for Tech Leaders Navigating What’s Now—and What’s Next

Tonya Turrell
  • 5.0 (6)
  • Technology
  • Updated Weekly

Between Fires and Futures is the podcast for modern tech leaders caught in the constant tension of today and tomorrow. It’s the space between daily firefights—cloud issues, AI hype, security breaches—and the visionary work of building scalable, resilient, future-ready organizations. Each week, we talk with the strategists, technologists, and innovators doing the real work of leading change. These are unfiltered conversations that expose the tradeoffs, wins, and lessons no one puts in the case studies. No spin. No fluff. Just pressure-tested leadership, real-world insight, and bold thinking. https://www.technologymatch.com/ 

  1. 2d ago

    Some of Your Vendors Need to Be Put on a PIP: The Vendor Performance Review Most CIOs Have Never Done with Knit.Ai’s Matt Glenn

    What happens when your technology vendors are underperforming, but your organization doesn’t have the data to prove it? In this episode of Between Fires and Futures, Tonya sits down with Matt Glenn, co-founder and CEO of Knit AI, to unpack a blind spot hiding inside many IT organizations: companies hold employees accountable for performance, but often spend millions of dollars with technology vendors without applying the same level of scrutiny. Drawing on experience from both sides of the vendor relationship, Matt explains why support quality can decline as technology providers prioritize growth and operational efficiency, and why IT leaders need better visibility into what their vendors are actually delivering. Matt explains why vendor performance is often buried across support portals, emails, individual interactions, and unreliable memories, leaving CIOs without the evidence they need when renewal and contract negotiations arrive. He shares what Knit has learned from analyzing more than a million vendor interactions, including how unresolved support cases, missed SLAs, product defects, and months of back-and-forth can quietly consume valuable engineering resources. Rather than relying on vendor-curated QBR data or how teams feel about a provider at the moment, Matt argues that organizations need a system of record that reveals performance over time. Tune in to hear:  Why technology vendors should be held to the same performance standards as employeesHow growing reliance on SaaS, cloud, and third-party technology has increased vendor riskWhy missed SLAs, product defects, and unresolved support cases quietly drain IT resourcesWhat more than a million vendor interactions reveal about the true cost of poor performanceWhy vendor-curated QBRs and customer reviews don’t always tell the full storyHow bringing objective performance data into vendor meetings changes the power dynamicWhy vendor data can help CIOs distinguish between a provider problem and an internal team problemHow performance trends can serve as an early warning system for long-term vendor decisionsWhy contract renewals and negotiations change when IT leaders have measurable evidenceHow vendor intelligence can help CIOs move from reactive problem-solvers to strategic businessImportant Links:  https://app.technologymatch.com/solutions/vendor-performance-management Website: knitit.ai LinkedIn: https://www.linkedin.com/in/matthewglenn/ Academic paper about the personality traits of people that work in it: https://www.ccsenet.org/journal/index.php/cis/article/view/36413

  2. Sep 28

    You Hired a Thousand Agents and Skipped Onboarding with Sumeet Vaidya

    What happens when AI helps your engineering team write code faster than your organization can actually test, validate, and safely ship it? In this episode of Between Fires and Futures, Tonya sits down with Sumeet Vaidya, co-founder and CEO of Crafting, to unpack a growing challenge inside AI-powered engineering organizations: coding velocity has accelerated, but the infrastructure needed to test, review, and validate that work hasn’t necessarily kept pace. Drawing on nearly a decade of engineering leadership experience at companies including Uber and Discord, Sumeet explains why adopting AI agents isn’t simply about giving teams new tools. It requires rethinking the systems, guardrails, and accountability structures surrounding the work those agents produce. Sumeet explains why organizations should stop chasing every new AI tool and instead take an outcomes-driven approach to adoption. He shares why engineering leaders should ask what would break if they suddenly had 10 times as many engineers, how hundreds or thousands of agents can make even a mid-market company operate with the complexity of a much larger organization, and why testing, validation, code review, coordination, security, and infrastructure can quickly become new bottlenecks. Rather than accepting that risk as the cost of moving faster, Sumeet argues that companies need to hold agents to many of the same standards they already use for human engineers. Tune in to hear: Why faster AI-generated code is shifting the bottleneck from writing to testing and validationWhat separates companies strategically adopting AI agents from those simply chasing the latest toolsWhy organizations shouldn’t accept untested AI output just because agents are moving fasterThe thought exercise every engineering leader should try: what would break if your team suddenly grew 10x?How hundreds or thousands of agents can make a mid-market company operate with enterprise-level complexityWhy testing, code review, infrastructure, security, and coordination can become hidden AI bottlenecksHow holding AI agents accountable like human engineers can unlock more valuable workWhy guardrails, identity, access, and authentication become critical as agents gain more autonomyThe risks of giving AI agents unrestricted access to company systems and sensitive informationHow better AI infrastructure can free people to focus on judgment, strategy, relationships, and uniquely human workhttps://app.technologymatch.com/vendor/solutions/f007e47c-fdbb-4d3d-a2a2-ecb4b739cb89

  3. Sep 21

    Hackers Just Went Machine-Speed, Your Defense is Still Human with Cyberhoot’s Craig Taylor

    What if the biggest cybersecurity threat facing your company is about to move faster than your team can respond? In this episode of Between Fires and Futures, Tonya sits down with Craig Taylor, co-founder of CyberHoot, to unpack a rapidly changing cybersecurity landscape where AI can discover software vulnerabilities at machine speed, dramatically shrinking the amount of time businesses have to protect themselves. With nearly three decades of cybersecurity experience and a background in psychology, Craig explains what this shift means for IT leaders, MSPs, and mid-market organizations trying to prepare without creating panic or burning out their teams. Craig breaks down five practical steps organizations can take now to reduce their exposure, including shrinking their internet-facing attack surface, accelerating patching, isolating or modernizing legacy systems, reducing unnecessary data storage, and improving early breach detection. He explains why traditional patching timelines may no longer be fast enough, how years of forgotten data can turn a security incident into a costly nightmare, and why leaders need to understand exactly which doors and windows into their environment have been left open. They also explore the human side of cybersecurity and why fear-based phishing tests may actually work against the behavior companies are trying to create. Craig shares how positive reinforcement, psychological safety, and hands-on learning can help employees build lasting cybersecurity habits. As AI changes both offensive and defensive capabilities, he explains why organizations need to strengthen their technology defenses while creating a culture where employees feel confident recognizing risks, reporting mistakes, and becoming an active part of the security strategy. Tune in to hear: Why AI-powered cybersecurity threats are moving from human speed to machine speedWhat the “months, not years” warning means for IT and business leadersFive practical steps companies can take now to prepare for AI-driven cyber threatsWhy reducing your internet-facing attack surface should be a priorityHow AI is changing the timeline between software patches and active exploitationWhy organizations may need to rethink traditional patching schedulesHow legacy systems can create hidden vulnerabilities and what to do about themWhy keeping decades of unnecessary data can dramatically increase the impact of a breachHow honeypots and early detection can help reduce attacker dwell timeWhy traditional “gotcha” phishing tests can undermine employee trust and engagementHow positive reinforcement can create stronger, longer-lasting cybersecurity behaviorsWhy psychological safety matters when employees make security mistakesHow AI-powered phishing is making personalized social engineering more convincingWhat IT leaders should prioritize this quarter to prepare for the changing threat landscapeWhy cybersecurity resilience requires both stronger technology and better-equipped peoplehttps://app.technologymatch.com/vendor/solutions/cyberhoot-vciso-services

  4. Sep 14

    Why Your IT Provider Keeps Letting You Down And Why It's Probably Not Their Fault — with Scott Raymer, Get IT Sense

    What if the IT provider you trust isn’t actually the problem—but the way IT support is structured is setting your company up to stay reactive? In this episode of Between Fires and Futures, Tonya sits down with Scott Raymer, founder of Get It Sense, to unpack why so many IT departments and managed service providers are stuck in constant firefighting mode—and what business and IT leaders should be looking for if they want to move from reactive support to proactive IT management. With more than two decades of experience consulting businesses on their technology needs, Scott explains why today’s IT challenges often come down to three critical areas: people, products, and processes. As cybersecurity threats, compliance requirements, data privacy concerns, and emerging technologies continue to evolve, the old “set it and forget it” approach to managed IT simply isn’t enough. Companies need clearly defined responsibilities, the right technology, proactive oversight, and providers willing to be held accountable for the service they promise. Scott also breaks down what leaders should demand before signing an IT contract, including clearly defined service level agreements, response and restoration expectations, escalation paths, reporting, and a regular cadence of strategic reviews. He explains why organizations shouldn’t assume they are secure simply because nothing has gone wrong yet—and why factual, current assessments are essential for uncovering the invisible risks that could lead to downtime, ransomware, compliance issues, or costly business disruption. They also explore how companies can strengthen an existing IT relationship without necessarily replacing a trusted provider, why cybersecurity and compliance require deeper expertise than many smaller IT teams can provide alone, and how emerging technologies like AI are making continuous education and modernization even more important. Scott shares why the IT solution that works today may not be enough six months from now—and what leaders can do to make sure their technology partners are prepared to evolve with them. Tune in to hear: Why so many IT departments are stuck in reactive firefighting modeThe three gaps behind many IT support problems: people, products, and processesWhy the traditional “set it and forget it” MSP model no longer worksHow invisible cybersecurity and compliance risks can become expensive business disruptionsWhat IT leaders should demand in writing from their service providersWhy clearly defined SLAs, escalation paths, and accountability matterThe red flags to watch for when evaluating a new IT providerHow to strengthen a trusted IT relationship when your current provider lacks depthWhy leaders need current, factual data before assuming their IT environment is secureHow AI and other emerging technologies are changing what companies need from their IT partnersImportant Links: https://www.getitsense.com/

  5. Sep 7

    The Cost of Intelligence: Why Your AI Bill Exploded While Tokens Got Cheap — with Dell's Allen Clingerman

    What happens when the cost of artificial intelligence keeps dropping, but your company’s AI bill keeps climbing? In this season three premiere of Between Fires and Futures, Tonya sits down once again with Alan Clingerman, Chief Technology Strategist and Partner AI Officer at Dell Technologies, to unpack the rapidly changing economics of enterprise AI and what IT leaders need to understand as they plan for the future. Alan explains why cheaper AI tokens aren’t necessarily translating into cheaper AI deployments. Longer context windows, agentic AI, data processing, cloud infrastructure, and increasingly complex workloads are creating costs that many organizations never anticipated. He also shares why companies that began experimenting with AI in the public cloud are now reconsidering where their workloads should live as those experiments move into production and scale. They also dive into the growing shift toward edge, core, and cloud strategies, why AI PCs could fundamentally change the economics of AI adoption, and how specialized models and intelligent AI routing may help organizations control costs without sacrificing performance. Alan also explains why getting your data architecture right remains one of the most important steps companies can take as they prepare for a future driven by agents. Tune in to hear: Why AI bills are rising even as token costs fallHow AI agents dramatically increase token consumptionThe hidden costs behind enterprise AI deploymentsWhy scaling cloud-based AI can create unexpected costsHow to decide where AI workloads should run across edge, core, and cloudWhy AI PCs could change the economics of AI adoptionWhy more organizations are bringing AI workloads back on-premiseHow smaller, specialized models can improve cost and performanceWhy data readiness is essential for successful agentic AIThe three moves mid-market IT leaders should make right nowImportant Links: https://app.technologymatch.com/solutions/dell-technologies-ai-factory https://app.technologymatch.com/solutions/dell-ai-pcs https://app.technologymatch.com/solutions/dell-ai-solutions https://app.technologymatch.com/solutions/dell-pro-ai-studio https://app.technologymatch.com/solutions/dell-pro-max-with-gb10 https://www.linkedin.com/in/clingerman/

  6. May 25

    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

  7. May 18

    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 behindConnect with Raheela: https://www.linkedin.com/in/raheelananji/ https://ree-consulting.com/

  8. May 11

    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

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About

Between Fires and Futures is the podcast for modern tech leaders caught in the constant tension of today and tomorrow. It’s the space between daily firefights—cloud issues, AI hype, security breaches—and the visionary work of building scalable, resilient, future-ready organizations. Each week, we talk with the strategists, technologists, and innovators doing the real work of leading change. These are unfiltered conversations that expose the tradeoffs, wins, and lessons no one puts in the case studies. No spin. No fluff. Just pressure-tested leadership, real-world insight, and bold thinking. https://www.technologymatch.com/ 

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