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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