Beating “Checkbox Security” With Continuous Offense with Sonali Shah

Beating “Checkbox Security” With Continuous Offense with Sonali Shah

Security doesn’t fail because you missed a tool, it fails because “secure today” tricks you into relaxing tomorrow. This episode exposes why the real fight isn’t compliance… it’s whether your defenses hold up once attackers hit you with machine-speed pressure.

Ron sits down with Sonali Shah, CEO of Cobalt, to talk about how human-led, AI-powered penetration testing is evolving into full-spectrum offensive security. Sonali shares how Cobalt can start a test in 24 hours, push findings directly into Slack/Teams and Jira, and use learnings from 5,000+ pentests a year to continuously sharpen what gets caught. The big takeaway: automation finds the easy stuff as humans find the business-logic traps and attack chains that actually break companies.

Impactful Moments 00:00 - Introduction 02:21- Sonali’s unexpected CEO path 06:10 - Compliance isn’t real security 10:19 - PTaaS: start in 24 hours 12:33- 5,000 pentests yearly scale 17:01 - Humans beat automation limits 20:16 - AI behavior vulnerabilities emerge 27:54 - Indirect prompt injection explained 30:51 - Why juniors + AI is risky 38:27 - 2026 becomes AI battleground

Links Connect with Sonali on LinkedIn: https://www.linkedin.com/in/sonalinshah/

Check out Cobalt: https://www.cobalt.io

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Episoder(412)

Turning Agent Chaos into a Command Center with Pedram Amini

Turning Agent Chaos into a Command Center with Pedram Amini

Text threads made AI feel personal, then agents made it productive, and suddenly “success” turns into chaos you can’t even track. In this episode, Ron sits down with Pedram Amini, creator of Maestro,...

10 Feb 37min

Why MFA Isn’t the Safety Net You Think It Is with Yaamini Barathi Mohan

Why MFA Isn’t the Safety Net You Think It Is with Yaamini Barathi Mohan

Phishing didn’t get smarter, it got better at looking normal. What used to be obvious scams now blend directly into the platforms, workflows, and security controls people trust every day. In this epi...

29 Jan 32min

When Cybercrime Learned How to Make Money and Never Looked Back with Graham Cluley

When Cybercrime Learned How to Make Money and Never Looked Back with Graham Cluley

Cybersecurity didn’t start as a billion-dollar crime machine. It started as pranks, ego, and curiosity. That origin story explains almost everything that’s breaking today. Ron sits down with Graham C...

25 Jan 37min

When Automation Outruns Control with Joshua Bregler

When Automation Outruns Control with Joshua Bregler

AI doesn’t break security, it exposes where it was already fragile. When automation starts making decisions faster than humans can audit, AppSec becomes the only thing standing between scale and catas...

18 Jan 37min

The Day AI Stopped Asking for Permission with Marcus J. Carey

The Day AI Stopped Asking for Permission with Marcus J. Carey

AI didn’t quietly evolve, it crossed the line from recommendation to execution. Once agents stopped advising humans and started acting inside real systems, trust replaced experimentation and consequen...

15 Jan 33min

When AI Ships the Code, Who Owns the Risk with Varun Badhwar and Henrik Plate

When AI Ships the Code, Who Owns the Risk with Varun Badhwar and Henrik Plate

AI isn’t quietly changing software development… it’s rewriting the rules while most security programs are still playing defense. When agents write code at machine speed, the real risk isn’t velocity, ...

8 Jan 35min

Think Like a Hacker Before the Hack Happens with John Hammond

Think Like a Hacker Before the Hack Happens with John Hammond

What if the most dangerous hackers are the ones who never touch a keyboard? The real threat isn't just about stolen credentials or ransomware; it's about understanding how attackers think before they ...

1 Jan 28min

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