---
title: "Chat with Jack · Brain Security"
description: "The bot that trains your workforce in the messaging apps: micro-lessons that show up on their own, signed Jack."
canonical: https://startbrain.io/en-gb/catalog/chat-with-jack/
lang: en-gb
---

# Chat with Jack

> The bot that trains your workforce in the messaging apps: micro-lessons that show up on their own, signed Jack.

Bot · SaaS · Slack (Teams and Google Chat coming later)

## Overview

**Chat with Jack** installs a character in your messaging apps: Jack, a teasing hacker turned ally, who sends everyone **5-minute conversational micro-lessons** by direct message.

Every lesson follows the same arc: a real attack story, the victim’s perspective, the signals to spot, two quizzes and three rules to remember. **30 lessons** cover phishing, social engineering, passwords, MFA, deepfakes, OSINT… plus a 12-episode narrative campaign.

No phishing simulation. Jack builds the **reporting reflex**: anyone can forward him a suspicious message. On the CISO side, a dashboard tracks completion, quiz accuracy and reports.

## Highlights

- **Native to the messaging app** : Slack, where your teams already work. Microsoft Teams and Google Chat coming later.
- **30 scripted lessons** : 5 minutes each, bilingual FR/EN, personalised (first name, company, executives).
- **Narrative campaign** : “The Rise of the Hacker”: 12 episodes in 4 acts, plus 2 branching gamebooks.
- **Reporting reflex** : Forwarding a suspicious message to Jack = a real behavioural signal, without simulation.

## By the numbers

- 30 Lessons
- 5 min Per lesson
- 2 Quizzes per lesson
- 12 Campaign episodes

## Specs

- Channels : Slack (native); Microsoft Teams and Google Chat coming later
- Cadence : Configurable: automatic drip, reminders, final diploma
- Languages : French, English
- Management : Dashboard: progress, quizzes, reports, CSV export

## Frequently asked questions

- **Why no phishing simulation?** Because the reflex that matters is reporting, not punitive distrust. Jack measures a real signal: the suspicious messages people forward to him.
- **How much of your teams’ time does it take?** 5 minutes per lesson, about one a month by default. The cadence is set per campaign.
- **Is the content AI-generated?** No: every lesson is scripted and reviewed. Jack’s voice is written, not improvised.

## Cyber Culture & Gamification

- [Social Engineering Training: Why Interactive Dialogue Beats Tip Sheets](https://startbrain.io/en-gb/cybersecurity/social-engineering-interactive-dialogue-training/): Discover how interactive dialogue training prepares employees to counter workplace messaging manipulation and social engineering attacks on Slack.
- [Prompt Injection: How Attackers Manipulate AI Assistants via Language](https://startbrain.io/en-gb/cybersecurity/prompt-injection-ai-assistant-security-risks/): What is prompt injection? Discover direct and indirect attack vectors on corporate LLMs and how to train your workforce against linguistic manipulation.
- [Autonomous AI Agents and Enterprise Connectors: Managing Emerging Risks](https://startbrain.io/en-gb/cybersecurity/autonomous-ai-agents-enterprise-security-risks/): Uncover security risks of autonomous AI agents linked to corporate tools, from indirect prompt injection to OAuth scopes and human training.

---

- https://startbrain.io/en-gb/catalog/chat-with-jack/
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- [llms.txt](https://startbrain.io/llms.txt)