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Bill Haber

Bill Haber

Co-founder & CEO of TEKRiSQ, a cyber risk firm helping SMBs and insurance advisors assess and build resilience to cybersecurity risk.

Sep 23, 2026

0:00
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
3:32
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?
3:39
Sure.
3:39
So we have some, uh, some unique views about that, Greg, and, uh, we're not afir-afraid to ruffle some feathers about that.
3:46
But, you know, we think the status quo of security questionnaires aren't always reducing risk and are perpetuating paper compliance.
3:56
We think that it's really important to replace these flat, self-attested checklists with more intuitive point-and-click branching risk assessments.
4:08
Um, we think it's important to provide context in business English that people relate to.
4:14
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

18:19
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?

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