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The Help Desk

Podcast door Ravenna Software, Inc.

Engels

Business

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Over The Help Desk

The Help Desk is the official podcast from Ravenna, where we dive into the future of work, AI, and internal support. Join us for candid conversations on building a startup, scaling operations, and automating the help desk with AI. Whether you're an IT leader, entrepreneur, or just curious about how modern teams work behind the scenes, this is your front-row seat to the workflows shaping tomorrow.

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aflevering No one cares about the Help Desk | John Matthews (CIO) artwork

No one cares about the Help Desk | John Matthews (CIO)

In this episode of The Help Desk, host Kevin Coleman sits down with John Matthews, legendary Seattle-area IT veteran, former CIO at F5 Networks and ExtraHop, and longtime Microsoft leader, for a candid, no-BS conversation about the future of IT, AI, and internal services. John pulls back the curtain on what it’s actually like to run technology at scale: why “all software kind of sucks,” why no one cares about the help desk until everything breaks, and why AI is both the most exciting and terrifying shift CIOs have faced in decades. Drawing from decades of experience, he shares practical guidance on how leaders should approach AI, not as a hype-driven cost-cutting exercise, but as a tool to grow capacity, empower teams, and make work suck less. You’ll hear John’s sharp takes on: * Why AI should be deployed first in low-stakes, high-impact operational workflows * The hidden power (and politics) of the help desk and ticketing systems * How CIOs can safely learn AI before rolling it out to revenue-critical teams * The “find it, fund it, fit it, fix it” framework for adopting new technology * Why automation should unlock growth—not just eliminate headcount If you’re a CIO, IT leader, or operator navigating AI pressure from the board while still trying to keep the lights on, this episode is packed with hard-earned wisdom, practical advice, and refreshingly honest perspective.

16 dec 2025 - 41 min
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