Ethical Hacker/Pentester Mid to Senior Level (5+ Years) - LATAM

Insight Assurance is a global audit firm on a mission to transform how organizations achieve cybersecurity and compliance. Founded by former Big 4 (EY) professionals, we deliver next-generation audit services across SOC 2, ISO 27001, PCI DSS (QSA), HITRUST, CMMC (C3PAO), and FedRAMP (3PAO) frameworks. We’re not your traditional audit firm — we’re tech-enabled, leveraging compliance automation and advanced collaboration tools to make audits faster, smarter, and more impactful for our clients. Recognized on the Inc. 5000 and Fast 50 lists, Insight Assurance is one of the fastest-growing global audit firms, with 170+ professionals supporting nearly 2,000 clients across the Americas, EMEA, and APAC. About the Role We are seeking a highly skilled and experienced Red Team Operator to join our cybersecurity team. The ideal candidate will be responsible for simulating advanced persistent threats (APTs), conducting adversarial assessments, and helping strengthen our organization's security posture. You will work closely with cross-functional teams, including blue teams, to identify vulnerabilities, test incident response mechanisms, and provide actionable insights to mitigate risks. Key Responsibilities Adversary Simulation : Plan and execute realistic attack scenarios simulating the tactics, techniques, and procedures (TTPs) of sophisticated threat actors. Design and deliver red team engagements, including physical, social engineering, and cyberattack components. Technical Assessments : Perform penetration testing of networks, applications, and systems using tools such as Burp Suite, Metasploit, Cobalt Strike, and custom scripts. Bypass defensive controls, including IDS/IPS, firewalls, EDR solutions, and WAFs. Exploit vulnerabilities to achieve and escalate privilege levels while avoiding detection. Reporting and Remediation : Prepare detailed reports documenting findings, attack vectors, and recommended mitigation. Present results to both technical and non-technical stakeholders. Collaboration and Knowledge Sharing : Collaborate with blue teams to refine incident detection and response capabilities. Provide guidance on improving threat hunting and monitoring strategies. Continuous Improvement : Stay updated on the latest attack techniques, vulnerabilities, and defensive countermeasures. Research and develop new tools, exploits, and methodologies to enhance the red team’s capabilities. Qualifications and Experience Experience : Minimum 5 years in offensive security, penetration testing, or red team operations. Technical Expertise : Proficient in scripting and automation using Python, PowerShell, Bash, or similar. Strong knowledge of Windows and Linux systems, Active Directory, and cloud environments (AWS, Azure, GCP). Familiarity with modern TTPs (e.g., MITRE ATT&CK framework). Certifications (Preferred) : Offensive Security Certified Professional (OSCP), Offensive Security Certified Expert (OSCE), GIAC Penetration Tester (GPEN), or other relevant certifications. Tools : Hands-on experience with Cobalt Strike, Metasploit, BloodHound, Impacket, Burp Suite, and other offensive security tools. Soft Skills Strong analytical and problem-solving skills. Ability to work independently and within a team. Excellent communication skills, both verbal and written. Critical thinking and creativity in approach to security challenges. Privacy Notice CCPA : Insight Assurance shares your personal data/information with Greenhouse recruiting because this is the tool we use for the recruitment process. Insight Assurance does not sell personal data/information under any circumstances. You may exercise your rights under personal data protection legislation by reaching out to us via: HR@insightassurance.com or submit a request via mail at 400 N Tampa St. 15th Floor Suite 122, Tampa, FL 33602 Privacy Notice GDPR: This notice informs you about the categories of Personal Data/ Information and the Purpose and Scope of Processing Activities to be undertaken by I…