Early Customer Signals and AI Experiments

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.

Behind the Scenes of Ravenna's First Launch Week

In this episode, Kevin and Tay break down Ravenna’s first-ever Launch Week, from prepping assets and designing a Miami Blade Runner inspired campaign, to releasing five major product updates in five days. They cover what went live (like Workflow Builder, Okta integration, and the Request Agent), how the team pulled it off, and why Launch Week is more than just a marketing moment, it’s a drumbeat of momentum, trust, and speed that defines the Ravenna brand.

Barbecue & Claude Code - Lessons Learned from our First Offsite in Austin

In this episode of The Help Desk, Kevin and Taylor recap Ravenna’s first company offsite in Austin — from sweaty weather and brisket-fueled bonding to the value of in-person time for remote teams. They dive into surprising use cases for Ravenna beyond IT, including how revenue and people ops teams are using the platform to automate repetitive internal requests. Finally, they geek out over Claude’s Cloud Code and how AI agents are transforming the way Ravenna builds (and dreams). Robots coding while you make breakfast? Yes, really.

Early Customer Signals and AI Experiments

In this episode, we dive into what’s been happening at Ravenna since the funding announcement. We discuss landing early customers, how the team uses Ravenna internally (bugs and all), and why building in public beats going stealth. We dive into some reflection on AI hype, a look at how Ravenna experiments with LLMs, and a healthy dose of “figuring it out as we go.”

Building in Public: The Ravenna Origin Story

Welcome to The Help Desk, a podcast about building Ravenna, the AI-powered help desk redefining internal support. In this episode, Kevin and Tay talk candidly about the origin of the company, why internal operations are an overlooked opportunity, and how AI is transforming IT, HR, and ops. If you're into startups, service management, or just want to hear how two friends decided to start from scratch (again), this one’s for you.