Sergio Medeiros

About Sergio Medeiros

As a Senior Penetration Tester on the Advanced Services team at Synack, I contribute to securing commercial and federal systems by uncovering and addressing vulnerabilities in web applications, APIs, and cloud environments. My expertise spans purple teaming, application security, and offensive security assessments, enabling organizations to enhance their detection and response strategies. Certifications such as OSEP, CRTE, eWPTXv2, eCPPTv2, and OASP underscore my commitment to advancing technical proficiency in this dynamic field. Previously, as a Security Analyst at Synack, I supported vulnerability validation and triage efforts, focusing on high-impact threats like SQL Injection, Remote Code Execution, and XSS. My achievements on the Synack Red Team include ranking in the U.S. Top 20 and earning recognition for reporting critical vulnerabilities. I remain passionate about advancing cybersecurity through hands-on research, collaborative engagements, and innovative problem-solving.

Experience

1. Senior Penetration Tester

   Synack

   Mar 2026 — Present · San Francisco, CA, US

   Lead advanced offensive security engagements across commercial enterprises and federal environments, delivering high-impact penetration testing services across modern application stacks, cloud platforms, and complex enterprise infrastructure. Partner with internal engineering and executive leadership to advance AI-assisted security testing capabilities and strengthen Synack’s go-to-market strategy- Lead complex offensive security engagements spanning web applications, APIs, mobile platforms, and cloud environments, performing both black-box and authenticated assessments for enterprise and federal clients- Lead AI-driven security testing initiatives, working closely with Synack’s AI engineering and leadership teams to design and optimize agent-based penetration testing methodologies, behavioral models, and offensive TTP frameworks for automated security assessment tooling- Contribute to Synack’s strategic innovation efforts, advising on how AI-assisted security technologies can enhance service delivery and support the company’s broader go-to-market strategy- Act as a technical lead during client engagements, guiding scoping, defining rules of engagement, and ensuring deliverables align with client risk priorities and business objectives- Design and execute red team and purple team exercises that emulate real adversarial tactics, techniques, and procedures (TTPs) to help organizations improve detection, response, and security operations maturity- Develop comprehensive penetration testing methodologies and tailored test plans, clearly defining objectives, scope, and execution strategy for complex security assessments- Deliver secure coding workshops and vulnerability training to Fortune engineering teams, focusing on real-world application vulnerabilities and secure software development lifecycle practices.

Education

• West Valley College

  Associate's degree, Computer Science

  2007

Skills

• Netsuite
• Data Mining
• Lead Generation
• Magento
• Online Sales
• Sales Process Development
• Salesforce.com
• Media Buying
• Affiliate Marketing
• Payment Card Processing
• Lead Development
• Solution Selling
• Cloud Applications
• Technical Product Sales
• Social Media Marketing
• Ppc
• Technical Sales Consulting
• Sales & Marketing Leadership
• Web Development
• SEO
• Sales Management
• Direct Sales
• Technology Integration
• Php
• Social Media
• Payment Industry
• Software as a Service (Saas)
• Business Development
• Digital Marketing
• E-Commerce
• Online Marketing
• Online Payment Solutions
• Development of Sales
• Yahoo Search Marketing
• Account Management
• Erp Implementations
• Customer Satisfaction
• Keyword Research
• Advertising Management
• Social Networking