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

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."

 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."

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

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.

In this episode of Agentless, Jason Loomis and Dave Cole dive into the ethical challenges that arise when CISOs partner with VCs and investors, particularly when financial incentives are involved. They explore the controversial "Gili Renan model," where CISOs allegedly receive kickbacks for promoting portfolio companies. The discussion touches on the transparency and moral obligations CISOs face in maintaining trust while participating in the startup ecosystem. They also address the complexities of balancing advisory roles with corporate responsibilities.

"If we paid CISOs more, the temptation for an extra 5,000 or 10,000 in equity wouldn’t be a factor. It’s about transparency and making ethical decisions that best serve the company, not personal gain." – Jason Loomis

"CISOs are instrumental to the startup ecosystem. But with that influence comes the need for transparency and a solid ethical framework. It's not just about defending the company—it's about trust." – Dave Cole

In this episode of Agentless: Jason and Dave dive into the mad, mad, Mad(Men) world of cybersecurity marketing, exploring what works and what doesn’t. They discuss the impact of well-timed, clear messaging in marketing campaigns, using Cylance's rise as an example. They also tackle the challenges of navigating overcapitalized markets, the importance of transparency in product documentation, and the role of community building versus traditional marketing tactics like golf outings, lampshade-clad models, and Ferrari driving events. The conversation bounces around in typical Dave (the thinker) and Jason (the...spaz??) fashion as they highlight the struggle for companies to stand out in a crowded market and the critical need for authenticity, both in marketing and product development.

"The product should sell itself. If I can't get into your documentation within three or four clicks, I'm out." – Jason Loomis

"If you want to do the same bullshit everyone else is, like golf events and Ferrari driving, it's going to be expensive and you're competing with everybody else. But if you're thoughtful and creative, you can do so much more with less." – Dave Cole

Welcome to the inaugural episode of "Agentless", the podcast. Hosted by long-time CISO Jason Loomis and seasoned and recovering security vendor Dave Cole, Episodes dives into the relationship between CISOs and vendors. Imagine Hollywood talent agents brokering deals between tech vendors (the studios) and over-caffeinated CISOs (the talent).

In this episode, we explore Cybersecurity conferences.  From RSA to  ShmooCon, we discuss the essential role of these events in the cybersecurity ecosystem. Nothing is off limits from the absurdities of virtual booths to the hefty price tags of real ones to the eternal frustration of salespeople who can't answer technical questions.