Insight On

Insight On is the podcast for leaders who make technology decisions — and need them to deliver. From CEOs and CIOs to the next wave of decision-makers in strategy, operations, and IT, you're invited into the inner circle of business and tech leadership. Each episode features a candid conversation or focused expert take exploring how real organizations across industries are choosing and using technology to drive results. Whether it's AI adoption, IT investments, or navigating change, Insight On gives you the insight you need before your next big decision.

Insight On is a technology podcast hosted by Insight Enterprises, with 46 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Insight Enterprises hosts Insight On, a technology show with 46 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #45

  Gen Z Has a Question for Employers — How Are You Using AI? | EP45

  Aug 11, 202638 minS2

  AI is reshaping entry-level work fast — and the generation walking into your workforce has already formed opinions about how you're handling it. Four college interns share what they actually think about AI, career development , and the skills that matter most when the task layer disappears. In this conversation, you'll hear why a company that doesn't use AI is a red flag to this generation, how AI freed up intern time for human connection rather than replacing it, and what one intern learned spending a summer as a formal test subject for AI-augmented entry-level work. If you're making decisions about headcount, hiring, or how to build AI confidence across your workforce, this one is worth your time. Check out Insight AI Flight Academy — the same gamified AI enablement program these interns experienced firsthand — because you'll see exactly how to build real AI adoption across your workforce : insight.com/ en_US /what-we-do/expertise/ai-flight-academy.html Want to go deeper on building an AI-ready team? " The AI Skills Playbook " walks through a five-step strategy for integrating AI into daily workflows: insight.com/ en_US /content-and-resources/gated/the-ai-skills-playbook-ac1402.html And if adoption is stalling in your organization, " AI Starts With Us " makes the case that AI success is a leadership challenge, not a technology one: insight.com/ en_US /content-and-resources/gated/ai-starts-with-us-drive-meaningful-ai-adoption-ac1393.html Subscribe to Insight On for more conversations with the people shaping how technology gets used at work. #AI #FutureOfWork #GenerativeAI #AIadoption #InsightOn Chapters 02:07 — How AI shaped their college experience 04:09 — Would you work for a company that doesn't use AI? 07:19 — AI skills coming into the internship 09:42 — Tasks AI made faster — real examples 11:12 — The validation problem — catching AI errors 12:44 — Did you learn more from AI or from people? 16:38 — Are you afraid AI will take your job? 21:48 — Advice for younger siblings entering the workforce 28:32 — What employers should do to support AI adoption 31:11 — Make the business case — why hire humans over AI?

  ListenShow Notes
• 

  Episode #44

  The Org Decision Most CFOs Are Too Cautious To Make | EP44

  Jul 28, 202652 minS2

  What does it actually take to move from AI adoption to AI transformation? It starts with a structural decision most organizations haven't made: giving someone AI transformation as their only job. Alex Pugh, d irector of f inance AI o perations at Insight, sits inside exactly that model — a dedicated AI ops team embedded within a single business function. This conversation gets into the accountability structures, the hard-won use case lessons, and the one metric that tells you transformation has worked ( it's not what you think) . Request a meeting with an Insight AI specialist to get t he rig ht framework for accountability structures that turn AI investment into measurable business outcomes: https://www.insight.com/en_US/what-we-do/expertise/data-and-ai.html Also worth your time: How T o S hift F rom R eactive to P roactive IT O perations: https://www.insight.com/en_US/content-and-resources/blog/how-to-shift-from-reactive-to-proactive-it-operations.html And, w hy prompting isn't the path to AI ROI: https://www.insight.com/en_US/content-and-resources/insight-on/the-product-manager-mindset-why-prompting-isnt-the-path-to-ai-roi.html If you're still in adoption mode and feeling stuck, here's h ow BlackLine successfully hit 99% Gemini adoption: https://www.insight.com/en_US/content-and-resources/case-studies/blackline-hits-99-adoption-of-gemini-enterprise-with-insight.html Subscribe for more conversations on AI strategy, IT modernization, and the decisions that separate leaders from the rest. # AItransformation #EnterpriseAI #InsightOn Chapters 00:00 — Welcome and introduction 05:36 — Why domain expertise beats pure AI expertise 08:02 — Dedicated AI team vs. distributed champion model 12:56 — Meet the Thundercats — Insight's dedicated finance AI ops team 16:07 — AI adoption vs. AI transformation — there's a difference 22:17 — The CFO's mission and the case for going all-in 25:20 — The bitter lesson and why waiting on AI is not a strategy 28:39 — How to find real AI use cases inside your organization 34:03 — Nine out of 10 use cases are not AI opportunities 46:26 — Rapid fire — worst advice, best metrics, and how you know it's working

  ListenShow Notes
• 

  Episode #43

  GitHub Copilot Usage-Based Billing: What To Fix | EP43

  Jul 7, 202644 minS2

  GitHub Copilot's billing model changed on June 1 — and most enterprise teams are about to see their first full bill under the new system. For many organizations, it'll be the first real look at what AI adoption actually costs at scale . The shift from flat-rate to usage-based billing sounds straightforward. Pay for what you use. But what your team is "using" turns out to be a lot more complicated than anyone expected — and the habits that felt like strong AI adoption six months ago are the same ones quietly running up the tab today. Sumner Ohye works with GitHub partners and enterprise customers across the Americas and APAC. And since June 1, h e's been fielding a lot of calls about billing . Parker Johnston is Insight's Agentic Field CTO — he's in the field with engineering teams every week. Together they get into what's happening on the ground, the common — and costly — mistakes people are making with token usage , and how teams are changing habits to keep token costs in check . There's a reason Parker opens with "you can no longer YOLO mode it" — and it's not just about prompting. Get GitHub Copilot solutions , available from Insight, because having the right partner means your billing controls, usage dashboards, and workflow guidance are in place before the charges hit — not after: https://www.insight.com/en_US/shop/partner/microsoft/github-copilot.html Want to go deeper on GitHub? Check out these resources from Insight: Burning Questions: Hot Takes on Developer Tools , AI , & What's Next: https://www.insight.com/en_US/content-and-resources/webinars/burning-questions-hot-takes-on-developer-tools-ai-whats-next.html What's New in GitHub Advanced Security: https://www.insight.com/en_US/content-and-resources/webinars/whats-new-in-github-advanced-security-key-updates-explained.html Maximizing Developer Efficiency W ith GitHub Enterprise: https://www.insight.com/en_US/content-and-resources/webinars/maximizing-developer-efficiency-a-guide-to-github-enterprise.html Strategies for GitHub Actions Optimization: https://www.insight.com/en_US/content-and-resources/webinars/strategies-for-github-actions-optimization.html Maximizing Team Productivity W ith GitHub Copilot: https://www.insight.com/en_US/content-and-resources/webinars/maximizing-team-productivity-with-github-copilot.html Subscribe for more episodes of Insight On: new conversations every week on AI, technology strategy, and what's actually working in enterprise tech. #GitHubCopilot #UsageBasedBilling #AgenticCoding Chapters: 03:25 — Is a 24x bill increase normal? What actually changed June 1st 05:38 — The transition period and what enterprises need to do now 07:14 — Agentic coding: when to use AI vs. doing it yourself 09:27 — Governing AI agents inside your codebase 11:24 — How to set up billing thresholds and avoid access shutdowns 13:28 — Why a third-party partner beats going direct to GitHub 17:11 — What the GitHub billing shift means for software development's future 18:20 — Running AI models locally vs. cloud: the real cost comparison 20:25 — How GitHub Copilot adoption has shifted since June 1st 21:43 — GitHub's evolution from source control to full agentic platform 25:34 — Building trust in agentic workflows: cost, security, and code quality 28:07 — The biggest mistakes teams are making with model selection and context 31:53 — Best practices for developers new to the GitHub Copilot environment 35:58 — How to measure ROI on agentic AI: DORA metrics, retention, and churn 37:54 — Real-world agentic use cases where the ROI still holds 40:57 — Code review automation: understanding the double billing reality

  ListenShow Notes
• 

  Episode #42

  Are Your Security Teams Ready for the New Patch Cycle? | EP42

  Jun 30, 20261h 6mS2

  The 90-day patch cycle was never perfect. But it worked because the window between a vulnerability being disclosed and an attacker building a working exploit was sufficient time for most organizations to respond. Frontier AI models like Anthropic ' s Mythos have closed that window. Now w e ' re talking hours. Possibly minutes . That ' s not a headline. That ' s the operating reality two of Insight ' s CISOs are already building security programs around. In this episode, Jeremy Nelson explains how frontier AI models don ' t just find vulnerabilities ; t hey build the exploit in the same process. He walks through the risk tolerance slider bar, a framework for understanding why the old patch cycle used to mak e sense bu t no longer does. And he shares the five questions every security leader should be able to answer right now ( the same ones your CEO and board are about to start asking ) . Jason Rader picks up where Jeremy leaves off . He ' s been having CISO-to-CISO conversations with clients who want to know how Insight is handling this . Why? N ot because everything is going smoothly, but because the honest account of what ' s working and what 's no t is more useful than a polished pitch. His answer to mid-market organizations facing the same threat surface as Fortune 500 companies — with fraction s of the resources — is direct: Leave behind security operations that aren ' t core to what you do and get visibility over everything else. Jeremy and Jason are operating with Insight as client zero , meaning Insight ' s own environment is where tools and programs are being proven before they 're offered to anyone else. Get Insight ' s Managed Exposure Defense because it ' s the same program built and battle-tested on Insight ' s own infrastructure — and it ' s available to organizations from one seat up: https://www.insight.com/en_US/what-we-do/expertise/managed-exposure-defense.html Also worth your time: The CISO Mythos Readiness Checklist: https://www.insight.com/en_US/content-and-resources/guide/the-ciso-mythos-readiness-checklist.html 5 Questions Every CISO Will Be Asked About Mythos: https://www.insight.com/en_US/content-and-resources/blog/5-questions-every-ciso-will-be-asked-about-mythos-and-how-to-answer-them.html Don't Hit Later on That Update Notification: https://www.insight.com/en_US/content-and-resources/article/dont-hit-later-on-that-update-notification.html Subscribe to Insight On for more conversations with the practitioners shaping enterprise technology strategy. #FrontierAI #Cybersecurity #CISO Chapters • 00:00 — Welcome and episode overview • 00:37 — Why the weaponization window has collapsed • 03:54 — How frontier AI models discover and create exploits • 08:18 — What to do when the threat feels overwhelming • 10:23 — Why your CMDB is your biggest security liability • 12:20 — Treating patch updates as security incidents • 14:22 — How AI fits into vulnerability management and defense • 16:48 — Inside Insight's managed exposure defense program • 18:42 — Extending protection to clients of all sizes • 20:14 — The risk tolerance slider — patching vs. business disruption • 24:16 — Why patch maintenance is now a permanent priority • 26:19 — Five questions every security leader must answer now • 38:12 — Jason Rader on being client zero and managed security services • 40:29 — What every business leader needs to know about Mythos • 44:13 — How frontier models operate inside your network • 47:04 — How Insight's security priorities have shifted • 48:07 — Mid-market security and the managed SOC advantage • 55:25 — Phishing risk when vulnerabilities go public • 57:43 — Zero days, patch ecosystems, and the hacker economy • 01:02:56 — The one thing every security leader must do tomorrow

  ListenShow Notes
• 

  Episode #41

  WestJet's Apple Device Program: A Client Story | EP41

  Jun 25, 202614 minS2

  WestJet crews used to carry their entire job s in heavy tote bag s — paper manuals, paper shift trades, policy updates inserted page by page. It was tedious, inefficient, and everyone knew it had to change. This is the story of what happened when WestJet went all-in on Apple devices across every cockpit and cabin. It's a story about a former flight attendant from a 500-person town in Newfoundland who became the person responsible for putting an iPad in every crew member's hand. A story a bout what goes wrong when your device vendor is in another country and keeps shipping the wrong thing. And a story about what " ready for takeoff" actually means when thousands of iPads are expected to work seamlessly before hundreds of daily flights. This episode is told in a narrative format — cinematic, human, and unlike anything we've done before on Insight On. Get Insight Flex for Device s, an AI-enabled Device as a Service (Daas) model because it can lower your total cost of ownership, automate lifecycle workflows, and enhance your employee experience : https://www.insight.com/en_US/what-we-do/expertise/digital-workplace/device-as-a-service.html Learn more about effortless Apple device management for the modern workforce: https://www.insight.com/en_US/content-and-resources/brands/apple/effortless-device-management-for-the-modern-workforce.html #DeviceLifecycleManagement #Apple #DeviceAsAService #WestJet #InsightOn

  ListenShow Notes

Recent guests on Insight On. Study who booked and why before you pitch.

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.