
Bill Haber
Co-founder & CEO of TEKRiSQ, a cyber risk firm helping SMBs and insurance advisors assess and build resilience to cybersecurity risk.
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APPEARANCES
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Sep 23, 2026
Short: Surprise! There's AI in your Enterprise with Bill Haber
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Bill HaberGUEST
And we've seen some unbelievable answers out of clients we engage where they say, "Oh, we have, you know, two main, uh, tools that we're using, uh, that have AI models in place." And we'll do a, a shadow AI check and realize, you know, you guys have 19 software apps that you are using across all of the, uh, the different employees, and we don't even know how many cloud-based ones there are, but we recommend that we find out, and they're shocked
The Vendor Trust Gap with Bill Haber
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18:19

Gregory RasnerHOST
Um, whether you love 'em or hate 'em, w-w-what do you feel about them in giving us a true picture of security from a vendor?

Bill HaberGUEST
So we have some, uh, some unique views about that, Greg, and, uh, we're not afir-afraid to ruffle some feathers about that.

Bill HaberGUEST
But, you know, we think the status quo of security questionnaires aren't always reducing risk and are perpetuating paper compliance.

Bill HaberGUEST
We think that it's really important to replace these flat, self-attested checklists with more intuitive point-and-click branching risk assessments.

Bill HaberGUEST
Um, we think it's important to provide context in business English that people relate to.

Bill HaberGUEST
We're all in our industry, you know, in our own heads, talking past vendors, and sometimes not aware that they just wanna, um, get through this really painful thing they don't quite understand and answer to the best of their ability, even if they don't know what you're talking about, and you end up with garbage if you're not really careful about that.
14 MINS LATER

Gregory RasnerHOST
Um, as, as vendors rapidly integrate AI tools and automated agents into their core platforms, how should organizations adapt their due diligence and continuous risk monitoring?