The IT Director's Podcast

Clear Winds Technologies

The IT Director's Podcast is for professionals who want to excel in their IT career. Every other Tuesday we provide answers and perspective to everyday IT solutions, giving you the know-how to excel in your IT career. Visit https://www.clearwinds.net/the-it-directors-podcast/ for show notes.

  1. Nov 3

    District Intelligence: Instant Answers for School Leaders

    District Intelligence puts attendance, grades, finance, and network data on one live dashboard for school district leaders. Imagine a superintendent answering a school board question on the spot instead of waiting weeks for a report. In this episode of The IT Directors Podcast, Jay and Michael sit down with Clear Winds CEO Stan Sargent to break down District Intelligence, a K-12 business intelligence platform powered by School Manager. Learn how the idea grew out of real cabinet meetings, how it correlates data from multiple systems, and why leadership teams see the value right away.This is a practical conversation for IT directors, superintendents, CFOs, and district cabinet teams who need faster, more accurate answers from the data they already have. 🚀 In this episode: • Learn how District Intelligence works as business intelligence for schools. • Hear how the idea came out of the report requests an IT director gets in cabinet meetings. • See how one dashboard breaks down siloed data across attendance, grades, finance, and network uptime. • Find out how insights and correlations connect academic, attendance, behavior, and device data. • Discover how it flags data that may not be right, including an attendance issue found in a proof of concept. • Learn why plain-English summaries and student-level drill-downs make reports easier to trust. • See how role-based access gives the superintendent, CFO, and MTSS team different views. • Hear how daily updates and state and national comparisons help leaders at school board meetings. • Find out how leaders can ask questions about their data by typing or talking. • Get the details on student data security, including a U.S. data center, SOC 2 Type 2, and what happens to a district's data if it leaves. If you're an IT director or district leader who is tired of scrambling for reports, this episode shows what District Intelligence can do with the data you already have. See the live demo at districtintel.com, then contact Clear Winds for a demo or a proof of concept using your own district's information. 🔔 Subscribe to The IT Directors Podcast: Get weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 👀 Check out the show notes: https://www.clearwinds.net/district-intelligence-the-it-directors-podcast/ 📲 Follow The IT Directors Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ X: https://x.com/itdirectorspod YouTube: https://www.youtube.com/@TheITDirectorsPodcast Apple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  2. Oct 20

    Cybersecurity Horror Stories: A $750K Email Scam

    Cybersecurity horror stories are real, and one spoofed email led to a $750,000 wire that was gone in about 60 seconds. In this episode of The IT Directors Podcast, Clear Winds CEO Stan Sargent shares the cybersecurity horror stories he has seen firsthand, and what IT directors can do before it happens to them. Jay and Michael sit down with Stan Sargent, CEO of Clear Winds Technologies, to walk through real cybersecurity horror stories. They cover a phishing click that led to ransomware months later, and backups that were encrypted along with everything else. This is a practical conversation for business owners, IT leaders, and technology professionals who want to understand how attacks actually unfold and what to do about them. 🚀 In this episode: - How a single phishing click turned into ransomware across a whole company - Why threat actors can sit in your network for six to nine months before they strike - The password file named “Passwords” and why password vaults and MFA matter - How offsite backups were encrypted too, and why you need to test your restores - Why EDR logs matter when you need to find out how attackers got inNTLM, pass the hash, and Kerberoasting explained - How a spoofed email led to a $750,000 wire transfer, and the phone call that prevents it - How stolen money can jump through five banks - Why student data is so fragile, and how K12 schools are approaching MFA - How AI is helping threat actors find vulnerabilities faster, and why quick patching matters - Why “we’re too small to be a target” is a myth If you’re an IT director responsible for protecting your company, these cybersecurity horror stories will help you spot the same weak points in your own environment. 🔔 Subscribe to The IT Director’s Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 👀 Check out the show notes: https://www.clearwinds.net/cybersecurity-horror-stories/ 📲 Follow The IT Directors Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ X: https://x.com/itdirectorspod YouTube: https://www.youtube.com/@TheITDirectorsPodcast Apple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  3. Oct 6

    How to Go From IT Pro to IT Director: 5 Skills You Need

    Most IT pros hit the same wall when they start trying to figure out how to become an IT director (or how to become an IT manager first): you've got the hard skills, you know the tech, but nobody ever taught you the other side of the job — the people, communication, and leadership skills that actually get you promoted, and keep you there once you land it. In this episode, Jay and Michael sit down to answer 5 real questions sent in by listeners and viewers about the leadership side of IT — the kind of questions that rarely get covered in technical training but matter the moment you start aiming for leadership. Jay and Michael pull from real moments across their own careers, including a story about a mail room employee who became pivotal to an entire organization's technology rollout — and what it taught them about the kind of leader worth following. This is a practical, no-BS conversation for IT pros, network engineers, developers, and anyone in tech who's ready to stop being just the "IT person" and start building the IT leadership skills and IT management skills it takes to move from IT manager to IT director. 🚀 In this episode: 0:00 Intro 2:09 How to delegate without micromanaging 6:56 How to translate tech language into business language 9:28 How to manage people across the organization 17:29 How to make quick decisions without all the information 24:00 How to have hard conversations 30:46 Outro If you've got the hard skills but nobody's taught you the other side of leadership — and you're trying to figure out how to become an IT manager or how to become an IT director — this episode is for you. 👀 Check out the show notes: https://www.clearwinds.net/how-to-become-an-it-director/ 🔔 Subscribe to The IT Director's Podcast: Weekly insights on how to become an IT manager, how to become an IT director, AI, cybersecurity, business IT strategy, business technology, automation, and the leadership skills that don't get taught anywhere else. 📲 Follow The IT Director's Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ X: https://x.com/itdirectorspod YouTube: https://www.youtube.com/@TheITDirectorsPodcast Apple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062 #HowToBecomeAnITDirector #HowToBecomeAnITManager #ITLeadership #ITDirector #ITManager

  4. Sep 22

    5 IT Director Skills EVERY Leader Should Know | Ep. 20

    Many IT directors eventually hit the same wall: you're great at the technical side, but no one taught you the actual IT director skills — the political, cultural, and leadership moves — that determine whether you thrive in the role or just survive it.In this episode, Jay and Michael sit down to answer 5 real questions sent in by listeners and viewers — the kind of questions that rarely get addressed in technical training but come up constantly for anyone leading an IT department. Jay draws on 25 years of experience as IT Director and COO at Birmingham City Schools, including a story involving a $21 million grant, Tim Cook, and a decision that almost went the other way.This is a practical, no-BS conversation for IT directors, CIOs, and anyone trying to lead a technology team while also navigating executive politics, retention, and burnout.🚀 In this episode:0:00 Intro1:48 How to get a seat at the executive table instead of just being "the IT guy"9:56 How to say no to a CEO's pet project without losing political capital16:52 How to manage a high performer who refuses to document anything19:17 How to retain great engineers when you can't compete on salary22:57 How do you actually unplug when you're the only one who understands the IT infrastructure29:24 BloopersIf you've ever felt stuck outside the room where decisions get made, or been the only one holding the keys to the kingdom — this episode is for you. 👀 Check out the show notes: https://www.clearwinds.net/5-it-director-skills-every-leader-should-know/🔔 Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and the IT director skills that don't get taught anywhere else.📲 Follow The IT Directors Podcast:LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/Instagram: https://www.instagram.com/theitdirectorspodcast/Facebook: https://www.facebook.com/theitdirectorspodcast/X: https://x.com/itdirectorspodYouTube: https://www.youtube.com/@TheITDirectorsPodcastApple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  5. Sep 9

    How to Mentor IT Teams and Troubleshoot Like a 50-Year Database Veteran

    Every IT team gets the same call: "the system is down." It's a description, not a problem — and the engineers who can tell the difference are the ones who keep systems running. In this episode, Jay and Michael welcome back fan favorite Rick Goudeau, employee number two at Clear Winds and a database specialist with over 50 years in technology dating back to the 1970s. Rick has spent his career on Oracle E-Business Suite upgrades, disaster database recoveries, and the kind of thorny problems that don't show up in vendor documentation. In "Tales From the Old Timer," he breaks down the specific behaviors that made him effective — thinking like a diagnostician, working methodically, staying relentlessly curious — and why mentoring the next generation is the part that lasts. This is a practical, no-BS conversation for IT directors, CIOs, DBAs, systems engineers, and anyone responsible for building a team that can troubleshoot without them in the room. 🚀 In this episode: - Why "the software doesn't work" is a description, not a problem — and how to get to the real issue - The Sherlock Holmes principle Rick has used for 50 years: eliminate the impossible, and notice the dog that didn't bark - Why being methodical doesn't mean being slow — and how documenting 200-300 step Oracle upgrades pays off years later - Why roughly 60-70% of IT problems are understanding issues, not technical ones - The WordPress fix that worked — and why the right engineer refused to stop at "it works now" - How an AI model change quietly slowed down a working application, and what that reveals about AI as a starting point vs. an ending point - Recovering a production database that was accidentally deleted — and the mentoring moment that came out of it - The reboot that didn't come back up, and why staying calm in front of the person shadowing you matters more than the fix - Why mentoring has to be organic, not something you do because you're a director or manager - The intern who bought Rick a mug 40 years ago — and why he's still using it - Rick's parents, two walls of books, and the reason he was never allowed to say "I'm bored" - Why the goal is building people who can pass you, not people who need you If you've ever been the only person who knew how to bring the system back up — this episode is for you. 👀 Check out the show notes: https://www.clearwinds.net/it-team-me... 🔔Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 📲 Follow The IT Directors Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ YouTube: https://www.youtube.com/@TheITDirectorsPodcast Apple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  6. Aug 25

    Russ White: Will AI Replace Network Engineers? (2026 Answer)

    Every network team is being told the same thing right now: automate faster or fall behind on AI. But the engineers actually getting it right aren't the ones automating everything — they're the ones who know exactly where automation can break things .In this episode, Jay and Michael sit down with Russ White, He has decades of experience building and designing large-scale networks for companies like Cisco, LinkedIn, and Juniper and holds the distinction of earning the very first Cisco Certified Design Expert (CCDE) certification in 2007. In addition, he hosts his own podcast, The Hedge. Russ White breaks down the real trade-offs of network automation, why AI should validate systems rather than build them, and whether AI will ever fully replace human judgment in network design. This is a practical, no-BS conversation for IT directors, CIOs, network engineers, and anyone leading AI or automation adoption inside an organization where one bad automated decision can take down the network. 🚀 In this episode: - Why "a fool with a bad tool is worse than a fool without a tool at all" - The hidden trade-off automation always brings: speed vs. brittleness - Why most automation failures come down to culture, not tools - How to shift a team's mindset from "build the runbook" to "hunt for new failure modes" - Why relying on AI to build systems — instead of validate them — is backwards - The Stanley Milgram experiment and what it reveals about blind trust in AI - What part of network engineering will always require humans, even in 2036 - Why humans' lack of self-discipline is the real AI risk, not the technology itself - What cloud, ATM, and expert systems can teach us about the current AI hype cycle - How Russ White's PhD in Philosophy shaped the way he approaches network design If you've ever been told to "automate everything" while still being the one responsible for the network staying up — this episode is for you. 👀 Check out the show notes: https://www.clearwinds.net/russ-white-will-ai-replace-network-engineers-2026/ 👀 Check out Russ White's podcast, The Hedge!: https://open.spotify.com/show/0LJ1ejpJIrnYeNJXYpWVe6 🔔 Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 📲 Follow The IT Directors Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ X: https://x.com/itdirectorspod YouTube: https://www.youtube.com/channel/UCj0XUY76X-5heKedsqHAEjQApple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  7. Aug 11

    How This University Cut an 11-Day Process to 2.7 Seconds With His AI Implementation Strategy

    Every university, hospital, and company is being told the same thing right now: move faster on AI or get left behind. But the leaders actually pulling it off aren't the ones chasing every shiny tool — they're the ones who know exactly which fights to avoid. In this episode, Jay and Michael sit down with Mike Mathews, Vice President of Global Innovation & Learning at Oral Roberts University, who's been leading AI strategy in higher ed since before most people knew what a chatbot was. He breaks down how ORU turned an 11-day manual process into 2.7 seconds, why "disruptive technology" is a phrase he refuses to use, and how they became the #1 ranked school in AI out of 11 competitive institutions — without putting their ERP system, network, or student data at risk. This is a practical, no-BS conversation for IT directors, CIOs, university administrators, and anyone leading AI adoption inside a large, complex organization where one wrong move can make headlines for all the wrong reasons. 🚀 In this episode: - Why the "AI love affair" is really 20 years old, not 2 - How to balance a 40-year-old ERP system with pressure to move fast on AI - The real story behind an 11-day process AI cut to 2.7 seconds - Why you should never call it a "chatbot" internally - The $300,000 question every organization faces when picking an AI platform - Why 25 years of IT spending has never actually gone down, despite every promise - The one AI experiment that failed — and what it proved about replacing people vs. systems - Managing 67 systems and thousands of AI agents without losing control - Why the future needs "AI maestros," not just certified admins - The one practical step to take before rolling out AI in your organization If you've ever been told to move faster on AI while also being responsible for not breaking anything — this episode is for you.👀 Check out the show notes: https://www.clearwinds.net/ai-implementation-strategy/ 🔔 Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 📲 Follow The IT Directors Podcast: LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/ Instagram: https://www.instagram.com/theitdirectorspodcast/ Facebook: https://www.facebook.com/theitdirectorspodcast/ X: https://x.com/itdirectorspod YouTube; https://www.youtube.com/@TheITDirectorsPodcast Apple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062

  8. Aug 6

    AI4 2026 Conference Recap: Geoffrey Hinton, AI Governance & Live Takeaways from Las Vegas

    Clear Winds went live from the floor of AI4 2026 in Las Vegas — the world's largest AI conference, with over 12,000 attendees from 100+ countries — to break down what's really happening in enterprise AI right now. In this episode, host Jay Bradford is joined by Clear Winds CEO Stan Sargent, VP of Engineering Michael Gray, and Director of Development James Hammack live from the show floor, fresh out of sessions with Geoffrey Hinton (the Nobel Prize-winning "Godfather of AI") and enterprise AI leaders from Global 500 companies. This is a real-time, no-BS debrief for IT directors, business owners, and anyone trying to cut through the AI hype and figure out what actually matters for their organization. 🚀 In this episode: Live reactions from the AI4 2026 show floor in Las VegasKey takeaways from Geoffrey Hinton's keynote on AI governance and steering vs. "hard-stopping" AIWhy this technology shift is fundamentally different (and more unpredictable) than past ones like virtualizationHow to treat AI agents like employees — identity, access, permissions, and loggingThe most common mistakes companies make when rushing AI implementationWhy messy or undefined data kills AI projects before they startWhat an AI readiness assessment actually looks forThe case for keeping a human in the loop, even as agents get more autonomousData sovereignty, security, and governance challenges every organization needs to plan for If you're trying to figure out how to safely and effectively bring AI into your business — or just want the real story from inside AI4 2026 — this episode is for you. 🎯 Timestamps:00:00 Live From Ai4 2026 In Vegas00:42 Ai4 2026 Show Floor Buzz01:08 Inside The Ai4 Vendor Hall01:46 AI Security Session Insights02:38 Steering AI Instead Of Stopping It04:12 What CEOs Tell Clients About AI06:02 Why This AI Shift Feels Different07:57 Hinton's Ai4 Keynote Breakdown10:40 AI Agents And Automation Tools11:43 Treat AI Agents Like Employees14:48 Why Humans Still Run The Show17:12 The Biggest AI Rollout Mistake20:56 Vegas Food And Conference Fun22:35 Final Thoughts Plus Where To Follow 🔔 Subscribe to The IT Director's Podcast: Weekly insights on AI, cybersecurity, business IT strategy, business technology, automation, and more. 📲 Follow The IT Directors Podcast:LinkedIn: https://www.linkedin.com/company/clear-winds-technologies/Instagram: https://www.instagram.com/theitdirectorspodcast/Facebook: https://www.facebook.com/theitdirectorspodcast/X: https://x.com/itdirectorspodYouTube: https://www.youtube.com/@TheITDirectorsPodcastApple Podcasts: https://podcasts.apple.com/us/podcast/the-it-directors-podcast/id1868490062 #AI4 #AI42026 #AIConference #ArtificialIntelligence #GeoffreyHinton #AIGovernance #AIAgents #ITLeadership #EnterpriseAI #ClearWinds

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About

The IT Director's Podcast is for professionals who want to excel in their IT career. Every other Tuesday we provide answers and perspective to everyday IT solutions, giving you the know-how to excel in your IT career. Visit https://www.clearwinds.net/the-it-directors-podcast/ for show notes.

Information

  • Creator
    Clear Winds Technologies
  • Years Active
    2026
  • Episodes
    24
  • Rating
    Clean
  • Copyright
    © Clear Winds Technologies
  • Show Website
    The IT Director's Podcast

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