CISO Series Podcast · Chai Podcast

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Episodes · 25

It's Not That We Don't Value Your Experience, We Just Don't Want to Pay for It

Jun 23, 2026 · 40m

Boards Love to Hear Jargon," Says Soon-to-Be-Fired CISO (LIVE in Boston)

Jun 16, 2026 · 48m

There's Nothing an LLM Can Screw Up That the Cloud Didn't Do First

Jun 9, 2026 · 44m

Our Data Security Policy Is Transparent in That It Doesn't Exist

Jun 2, 2026 · 37m

If You Love Cloud Misconfigurations So Much, Why Don't You Marry Them!

May 26, 2026 · 40m

Why Be Responsible When We Can Just Blame AI?

May 19, 2026 · 41m

Can You Please Train the AI on Your Way Out the Door?

May 12, 2026 · 36m

AI Confidence: It's a Trap! (LIVE in San Francisco)

May 5, 2026 · 43m

Step 1: Deploy New AI Tool. Step 2: Discover Security Flaws. Step 3: Repeat. (LIVE in Orlando)

Apr 28, 2026 · 42m

Back in My Day, You Could Get a Cybersecurity Job at the Corner Store

Apr 21, 2026 · 39m

Our Theoretical Controls Work Great Against Hypothetical Attacks

Apr 14, 2026 · 43m

Remember, Every Underappreciated Risk Is Just a Crisis Waiting to Be Discovered

Apr 7, 2026 · 42m

Do You Think These Compliance Boxes Check Themselves? (LIVE in Clearwater, FL)

Mar 31, 2026 · 43m

Why Highlight Diversity When We Can Just Hope You Don't Notice?

Mar 24, 2026 · 38m

They're Less "Best Practices" and More "Sounds Good on LinkedIn"

Mar 17, 2026 · 41m

It's Okay to Put All Your Eggs in One Basket as Long as You Really Trust the Basket

Mar 10, 2026 · 48m

Our Security Team's Love Language is Buying New Tools

Mar 3, 2026 · 41m

If We Can't Do Better, at Least Do It Faster

Feb 24, 2026 · 41m

We Gave the CISO Risk and Liability, and Now They Want Authority. The Nerve.

Feb 17, 2026 · 42m

When We See White Smoke, We Know We Have a New CISO

Feb 10, 2026 · 42m

Take Two-Factor Authentication and Call Me in the Morning

Feb 3, 2026 · 38m

I'll Show You Our Resilience Plan Once Our Cloud Storage Is Back Online

Jan 27, 2026 · 37m

AI Is Very Efficient at Making Us Forget the Value of Humans

Jan 20, 2026 · 41m

Managing Risk Has Been a Priority Ever Since You Asked About It (LIVE in NYC)

Jan 13, 2026 · 40m

Imagine Scaling Mistakes 5x Faster. Thank You, Automation! (LIVE in NY)

Jan 6, 2026 · 43m