---
title: "Securing the Agentic Enterprise"
description: "Jonathan Jaffe, CISO at Lemonade, on how to build, secure, and operate AI systems when both defenders and attackers are automated."
categories: ["office hours","AI security","enterprise"]
keywords: ["AI security","agentic enterprise","Jonathan Jaffe","Lemonade","Office Hours","Theory Ventures"]
ai_summary: "Jonathan Jaffe, CISO at Lemonade, on how to build, secure, and operate AI systems when both defenders and attackers are automated."
date: 2026-05-08
lastmod: 2026-08-05
canonical_url: https://www.tomtunguz.com/jonathan-jaffe-office-hours/
author: "Tomasz Tunguz"
---


{{< email_image src="fd77nwl2pbgrvlmmyum1" alt="Jonathan Jaffe, CISO at Lemonade" width="540" height="289" >}}

Enterprises run on AI agents. So do the attackers.

What does it mean to build, secure, and operate AI systems when both sides - defenders and attackers - are automated?

[Jonathan Jaffe](https://www.linkedin.com/in/jonathanjaffe/), CISO at Lemonade, is one of the most forward-thinking security leaders in this age of AI, with more than 25 years of experience in technical security roles since 1997.

Join us for a conversation covering :

- **When the attacker is an agent, the defender must be too.** Traditional security playbooks assume human adversaries at human speed. AI agents require AI defenders by design.
- **Agentic security as a systems problem.** How to build, monitor, and operate AI in the enterprise when both sides are autonomous.
- **Trust and oversight at machine speed.** Where to draw the line between automation and human judgment when adversaries act in milliseconds.

**The format.** 15 minutes online. One topic. Call-in questions live. No slides. No pre-written questions. Just a real conversation.

[Register here for Office Hours : Securing the Agentic Enterprise with Jonathan Jaffe](https://gatsby.events/theory-ventures/rsvp/register?e=office-hours-securing-the-agentic-enterprise).

[Apple Podcasts](https://podcasts.apple.com/us/podcast/office-hours-with-tomasz-tunguz) | [Spotify](https://open.spotify.com/episode) | [YouTube](https://www.youtube.com/watch?v=)