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Head of Security

Job in Cape Town, 7100, South Africa
Listing for: Chosen Online Pty Ltd
Full Time position
Listed on 2026-05-26
Job specializations:
  • IT/Tech
    Cybersecurity, Security Management & Operations
Job Description & How to Apply Below

R140 000, 00 per month depends on level and experience.

Location: Somerset West

Reports To: CTO / CEO

Employment Type: Full-time

About My Exclusive Client

My Exclusive Client is a leading integration and automation platform built on the .NET stack, empowering businesses to connect systems and streamline operations. We’re committed to building secure, resilient software and are seeking a visionary Head of Security who combines deep engineering expertise with cutting‑edge AI‑driven security practices.

Role Overview

We are seeking a Head of Security who operates like an ethical hacker and software engineer in equal measure. This is a hands‑on, dedicated role focused on proactively finding vulnerabilities
, securing operational controls
, and building AI‑augmented security solutions within our .NET codebase.

You will work primarily at the application layer, identifying attack surface points across the app and broader Microsoft Azure stack
, and designing/software‑engineering solutions to fix them. You’ll leverage AI effectively
—prompting it correctly to detect issues, generate secure code, and automate vulnerability discovery.

This is not a purely managerial role. You will write code
, build security tooling
, and engineer solutions directly into My Exclusive Client's platforms.

Key Responsibilities 1. AI-Driven Vulnerability Discovery
  • Use AI tools and large language models (LLMs) to systematically scan, analyze, and identify vulnerabilities in our .NET codebase
  • Craft precise prompts and develop AI‑assisted workflows to detect security flaws, insecure patterns, and logical loopholes
  • Build internal AI‑powered security scanners and automation tools
2. Ethical Hacking & Code-Level Security
  • Act as an ethical hacker within the codebase: perform deep code reviews, penetration testing, and exploit simulation
  • Identify security loopholes at the proxy layer
    , network layer
    , and infrastructure layer (not just application-level)
  • Map and analyze attack surface points across the Microsoft security stack (Azure, Entra , Defender, Sentinel, Key Vault, etc.)
3. Solution Engineering
  • Build software solutions (tools, patches, hardening frameworks) in .NET to remediate identified vulnerabilities
  • Design and implement operational security controls that are sustainable, automated, and measurable
  • Engineer secure‑by‑default patterns into My Exclusive Client's development lifecycle
4. Operational Controls & Security Strategy
  • Maintain and extend compliance certifications (e.g. SOC 2 Type II) by defining and enforcing security operational controls across development, deployment, and runtime environments
  • Conduct risk assessments and threat modeling focused on application, API gateways, and Microsoft Azure infrastructure
  • Develop incident response playbooks and proactive defense mechanisms
5. Collaboration & Culture
  • Work closely with engineering teams to embed security into the SDLC
  • Foster a “peaceful,” proactive security culture focused on discovery and prevention rather than blame
  • Mentor developers on secure coding practices, AI‑augmented security, and .NET security patterns
What You’ll Build
  • Detect and patch application‑layer vulns, working with the R & D team
  • Develop, test and review appropriate configuration for infrastructure
  • Custom security tooling integrating AI prompts, .NET code analysis, and Microsoft stack hardening
  • A proactive security culture where vulnerability discovery is celebrated, not punished
Required Qualifications Technical Skills
  • 5+ years in security engineering, ethical hacking, or application security
  • 3+ years as a software engineer with strong expertise in the .NET stack (C#, ASP.NET Core, Entity Framework)
  • Deep hands‑on experience with API gateways
    , reverse proxies
    , and general network security
  • Proven ability to use AI/LLMs for security
    : prompt engineering, automated code analysis, vulnerability generation/detection
  • Experience building security tooling
    , scanners, or automation frameworks
Certifications (Preferred but not mandatory)
  • OSCP, OSCE, or CEH (ethical hacking)
  • Microsoft certifications: AZ-500 (Security Engineer), SC-900/200
  • CSSLP, CISSP, or CISM (security leadership)
Soft Skills
  • Exceptional problem‑solver with a calm, methodical, and peaceful mindset
  • Strong communication skills to translate technical risks into actionable engineering tasks
  • Self‑starter who thrives in autonomy and takes ownership of security outcomes
What We Offer
  • A dedicated, focused role with minimal bureaucracy and maximum impact
  • Opportunity to pioneer AI‑driven security engineering in a real‑world .NET platform
  • Competitive salary + benefits
  • Continuous learning budget (confidence in AI, security conferences, certifications)
  • Trust‑based culture focused on building and preventing, not reacting
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