Meeting assets for SIP Study Group - 18th September 2025

Quick recap

Winton introduced a new presentation format focused on prompt databases and AI utilization, particularly with LLMs like ChatGPT, and shared details about the Safer Internet Project website and his role as program director of Asaka Hawaii. He demonstrated various AI prompt frameworks and systems, including a Notion-based prompt database and a text prompt system using the CRISP-E framework for LinkedIn profiles. The session concluded with Winton providing guidance on resume optimization for information security roles and presenting a system for effective prompt engineering using ChatGPT.

Next steps

• Attendees to create a Notion account if they don't have one already to follow along with the prompt database demonstration.
• Attendees to explore the prompt frameworks shared during the session for their own prompt creation.
• Attendees to build their own prompt database/library system to collect effective prompts.
• Attendees to test the cold networking email template shared during the session.
• Attendees to visit learn.saferinternetproject.com to access additional resources.
• Interested attendees to reach out to Winton via LinkedIn for potential discount codes for SIP membership.
• Attendees to consider booking a free 15-minute consultation call with Winton to discuss their goals.

Summary

AI Prompt Database Presentation

Winton introduced a new unconventional presentation format focused on prompt databases and AI utilization, particularly with LLMs like ChatGPT. He demonstrated a Notion-based prompt database and discussed the Safer Internet Project (SIP) website, which offers various resources including live sessions, study groups, and pre-recorded content for cybersecurity education and career development. Winton mentioned his role as program director of Asaka Hawaii and his upcoming availability as a mentor through the platform.

Cybersecurity Platform Introduction and Benefits

Winton shared his positive experience with the cybersecurity community platform and introduced the team members including David, Rio, Ange, and Rohit. He explained the platform's offerings, including CTFs, evolving courses, mentorship programs, and coaching services across various pathways like defensive, offensive IT freelancing, and cybersecurity fundamentals. Winton encouraged attendees to reach out with feedback and offered a potential discount code for membership through LinkedIn, highlighting that even a one-month membership would provide significant value.

Effective Prompt Database Management

Winton led a session focused on maintaining and utilizing a prompt database or library effectively. He demonstrated a newly created database structure in Notion, which includes columns such as purpose and type to help organize prompts. Winton emphasized the importance of keeping the database up-to-date by archiving unused prompts and maintaining only the most relevant and useful ones. He also highlighted his personal approach to documentation, attributing it to his memory challenges and desire for organization.

LinkedIn AI Prompt System Implementation

Winton discussed the implementation of a text prompt system using the CRISP-E framework, focusing on copywriting for LinkedIn profiles targeting recruiters. He explained how to track prompts using a spreadsheet with columns for AI app details, creation dates, and performance scores (1-5). Winton provided an example of using the framework to create a LinkedIn about section for cybersecurity professionals transitioning to AI roles, outlining the context, role definition, and input materials needed.

AI Prompt Frameworks and Applications

Winton presented various AI prompt frameworks including CRISPR, RICE, and others, demonstrating how they could be used for different use cases. He showed examples of how these frameworks could be applied to tasks like resume optimization and cold email outreach, emphasizing the importance of having clear context, language, expectations, and expected outcomes. Winton also discussed the need to build a personalized prompt library with tags for easy organization and retrieval of useful prompts over time.

Crafting Effective Networking Emails

Winton demonstrated how to write a cold networking email, focusing on creating a professional yet personable message to connect with an AI engineer. He showed different variations of the email, from very formal to more casual, emphasizing the importance of matching the tone to the recipient's communication style. Winton ultimately preferred a balanced approach that expressed admiration for the recipient's career path while respectfully requesting a brief virtual coffee chat to learn from their experiences.

Networking Emails and Resume Optimization

Winton demonstrated a method for creating and testing cold networking emails, scoring them based on response rates, and discussed a framework for parsing job postings to extract key information for resume optimization. He explained a two-part approach: first analyzing job requirements to understand what skills are needed, then comparing those requirements to a person's resume to identify gaps. Winton used a specific job posting example for an INFOSEC Analyst position to illustrate how to structure the parsing process and extract relevant keywords like INFOSEC Analyst, Cybersecurity, and GRC.

Optimizing Security Roles Resumes

Winton provided guidance on resume optimization for information security roles, emphasizing the importance of including relevant keywords to pass ATS scanners. He outlined required qualifications including 1-3 years of experience, a bachelor's degree in IT or related field, and understanding of security principles and technologies. Winton explained key security concepts using analogies, describing firewalls as security guards, VPNs as private tunnels, and antivirus as home pest control systems. He also covered various security frameworks like ISO 27001, NIST, and CIS controls, explaining them as playbooks or guidelines for proper information security management.

Optimizing Resumes and ChatGPT Prompts

Winton discussed resume optimization strategies, advising against adding irrelevant keywords and emphasizing the importance of accurately representing one's experience. He explained that the first 3-5 responsibilities listed in a job description typically represent 80% of the work, and highlighted key security-focused responsibilities including incident investigation, stakeholder collaboration, and ongoing security initiatives. The session concluded with Winton presenting a system for effective prompt engineering using ChatGPT, demonstrating how to create and refine prompts by understanding the intended audience and using a structured database of elements and attributes.