Agentless - Season 1 Episode 5

Agentless - Season 1 Episode 8 - Partnershits...ahem...ships

Listen in as Jason and Dave dive into the complexities of CISO-vendor relationships, exploring the nature of “partnerships” that are often presented as collaborative, but are often anything but in practice. We discuss the challenges of superficial “partnership” claims from vendors, the pitfalls of neglecting thorough vetting processes for real partners, and the emerging role of AI in transforming traditional partnership dynamics. "When vendors say ‘We see you as a partner,’ my advice to CISOs? Use that to your advantage. At the end of the day, this is a buyer-seller relationship—don’t mistake it for more." - Jason Loomis "Imagine a future where AI takes the reins on integration—it's 'Service as Software,' not 'Software as a Service.' We’re talking seamless connections without the messy human errors." - Dave Cole

Agentless - Season 1 Episode 7 - Product Pricing

Ever wonder why software pricing feels like the Wild West? In this episode, @JasonLoomis and @DaveCole break down the inconsistencies in vendor pricing and offer practical tips on negotiating smarter. Tune in to learn why you should never sign a 3-year deal and how to turn the tables by partnering with vendors. A must-listen for CISOs and anyone involved in tech procurement. Jason Loomis: "You don’t need a 3-year deal—make the vendor earn your business every year. Things change too fast to lock in pricing now." Dave Cole: "The more competitive your process, the better deal you’ll get. Vendors know their pricing is built on 'pixie dust and unicorn tears.' Use that to your advantage."

Season 1 Episode 6 - AI

In the latest Agentless Podcast, @JasonLoomis and @DaveCole dive into the AI hype cycle, comparing it to past tech fads like Y2K and the internet boom of the 90s. From the challenges CISOs face with AI to what companies need to prioritize, it's a must-listen for anyone navigating the evolving tech landscape. Tune in to hear why AI might not be ready to solve all your problems... yet." Jason Loomis: "AI is not ready yet. Put a magnifying glass on anyone selling you AI solutions—it's more hype than reality. Focus on the basics, like data governance and risk management." Dave Cole: "In times of profound change, teaching people how to think about AI is far better than imposing rigid policies. First principles will always win out over the hype."

Agentless - Season 1 Episode 5

On our latest episode of Agentless, we dive into the challenges of aligning vendor promises with reality, the importance of showing immediate value, and the frustrations both sides experience during the sales process - especially around POCs and Vs.  "Proving the concept is one thing, but showing value that makes a CISO reach for their wallet? That’s when you know you've hit the mark." – Dave Cole "It's not just about proving the tech works; it's about showing that it works in my environment. And 75-80% of POCs fail to do that." – Jason Loomis

Agentless Season1 Episode 4

n this episode of Agentless, we focus on the changing role of analysts, particularly in the cybersecurity space, and the evolving ways professionals gather trusted information. Listen in as Jason and Dave reflect on how analyst firms like Gartner have shifted from being a key resource in the '90s to a more commercialized model today. They also discuss alternative sources of advice, from VCs to AI tools like ChatGPT, and how these changes impact the vendor-CISO dynamic.