Offensive Security Engineer/Lead

Founded to transform retail finance, Ajaib Group is an Indonesian fintech unicorn breaking barriers to financial access. Having recently secured a $270M Series C—the single largest funding round in Southeast Asia over the past four years—we are backed by premier global investors including Y Combinator, Ribbit Capital, SoftBank, and SBI Holdings. To build world-class products, we assemble world-class talent. Supported by our fully remote work arrangement, our team spans Eastern Europe, the Middle East, India, and Southeast Asia, allowing you to work with brilliant engineers and builders from around the globe from wherever you are. We operate with an impact-driven purpose where everyone is the owner of our customers' satisfaction. Driven by a growth mindset and a fierce will to win, we refuse to settle and constantly push engineering boundaries. Role Overview As the Offensive Security Engineer/Lead, you will spearhead our adversarial simulation, penetration testing, and vulnerability research programs to proactively identify and neutralize security weaknesses. Reporting directly to the Head of Security, you will design and execute sophisticated Red Team campaigns, simulate real-world cyber adversary behaviors, and validate our detection capabilities. You will be responsible for operationalizing threat intelligence by mapping all simulation activities directly to the MITRE ATT&CK framework and the Lockheed Martin Cyber Kill Chain. Key Responsibilities Offensive Security Program Leadership: Define the strategy, scope, and execution roadmap for enterprise-wide penetration testing, red teaming, and adversary simulation exercises. Adversary Simulation & MITRE Mapping: Design and execute complex, multi-stage red team operations that emulate real-world Threat Actors and Advanced Persistent Threats (APTs), meticulously mapping techniques to the MITRE ATT&CK Framework. Cyber Kill Chain Validation: Evaluate the efficacy of our security posture across every phase of the Lockheed Martin Cyber Kill Chain (Reconnaissance to Actions on Objectives), identifying gaps in boundary defenses and internal monitoring. Purple Teaming Collaboration: Partner closely with the Blue Team (SOC and Incident Response) to conduct Purple Team exercises, using simulation data to refine detection engineering, SIEM alerts, and response playbooks. Vulnerability Exploitation & Reporting: Safely exploit vulnerabilities across network infrastructure, cloud environments, and applications. Translate complex technical proof-of-concepts into actionable, risk-prioritized remediation reports for engineering teams. Tooling Innovation: Oversee the development, deployment, and safe operation of proprietary offensive security tools, scripts, and command-and-control (C2) frameworks. Requirements Experience: 8+ years of dedicated technical experience in offensive security, ethical hacking, or penetration testing, with at least 2+ years leading a red team or offensive security function. Framework Expert: Mastery of the MITRE ATT&CK matrix (Enterprise, Cloud, and Mobile) and deep conceptual understanding of the Lockheed Martin Cyber Kill Chain methodology. Technical Environment: Proficient with commercial and open-source offensive tools (e.g., Cobalt Strike, Burp Suite, Metasploit) and deep familiarity with cloud-native security landscapes (AWS, GCP, or Azure). Scripting & Exploitation: Strong scripting/programming skills (e.g., Python, Go, PowerShell, Bash) to automate attacks, bypass security controls, and develop custom exploits. Certifications: Possession of advanced offensive security certifications such as OSCE, OSEP, OSWE, GXPN, or CRTO (Certified Red Team Operator) is highly preferred. Communication: Exceptional communication skills with a proven track record of explaining complex attack vectors and business impacts to both deeply technical engineers and non-technical business executives. Benefits Performance Bonus - Get rewarded for the impact you make Private Insurance - Comprehensive health coverage for you Paid Time Off - Take the time you need to recharge and come back stronger Learning & Development - Company-sponsored training, courses, and professional certifications Hybrid Work Arrangement - Enjoy the flexibility of working both remotely and from the office Career Growth - Work closely with experienced leaders and take on meaningful ownership as we scale Employee Perks - Enjoy exclusive discounts, partnerships, and lifestyle perks Collaborative & High-Ownership Culture - Work with smart, driven people in cross-functional teams, take ownership, and make a meaningful impact for our users.