Security leaders remain concerned about data breaches, with the global cost of cybercrime projected to reach $10.5 trillion annually by 2025. To address this threat landscape, software security teams employ proactive security approaches like penetration testing and red teaming. Penetration testing is a security assessment method where human testers examine systems for vulnerabilities against a predetermined methodology, usually for compliance with internal or external controls. Red team engagements involve simulating real-world attacks against an organization's technology, people, and processes, typically lasting 2-4 weeks for targeted assessments and 1.5-6 months for full-scale assessments. Both approaches offer benefits, including coverage, cost-effectiveness, and providing stakeholder reassurance, making them valuable tools in improving security posture. Red teaming accelerates an organization's security testing by identifying critical attack paths that cause the most damage, typically resulting in a 25% reduction in security incidents and a 35% reduction in the cost of security incidents. Combining penetration testing with red team engagements elevates security maturity by providing a comprehensive approach to securing systems against common and sophisticated vulnerabilities.