What does a Head of Security actually do?

People underestimate all the things a security leader has to do, let's clarify

May 25 • Ayman Elsawah

1

Strategy For Enabling Safe AI Usage

A 4 tier plan on enabling AI safely in the workplace

May 18 • Ayman Elsawah

2

Are Assessments Dead? Should Infra report to the CISO? Copilot pauses new signups! Is AGI here?

Adrian Sanabria, Jason Haddix, Ross Haleliuk and more

May 4 • Ayman Elsawah

2

1

April 2026

Don't Be An NPC

An brief essay on the future of jobs and work

Apr 20 • Ayman Elsawah

3

1

2

March 2026

How to Hire a CISO or Head of Security For High Growth Startups

I’ve had the privilege of working with high growth startups for 7 years now, functioning as a Head of Security, Dir of Security, Deputy CISO, CISO…

Mar 9 • Ayman Elsawah

2

1

The AI + Security Issue

Is AI to blame for vibe coded security issues?

Mar 1 • Ayman Elsawah

4

3

1

February 2026

Defining Risk

We all use the term, but have we stopped for a moment to try and understand what it really means?

Feb 17 • Ayman Elsawah

2

September 2025

It’s Time To Shift ZERO

Forget shift left. With AI we can now Shift ZERO.

Sep 18, 2025 • Ayman Elsawah

3

2

July 2025

The Good, The Bad, and The Ugly of vCISO Life

The Good, The Bad, and The Ugly of Fractional CISO Life

Jul 6, 2025 • Ayman Elsawah

1

1

May 2025

RSAC 2025 Recap

Innovation Sandbox winners and early thoughts on AI

May 5, 2025 • Ayman Elsawah

1

April 2025

Jokes On Us 🤣

This April Fool’s totally surprised me.

Apr 3, 2025 • Ayman Elsawah

March 2025

Avoid Root Canals In Security

Table of Contents

Mar 3, 2025 • Ayman Elsawah