Senior Penetration Tester - Remote Cybersecurity Expert
About the Role
We are looking for a Senior Penetration Tester remote to join our cybersecurity practice and lead high-impact security assessments across web, mobile, and network environments. In this role, you will simulate real-world attacks, uncover critical vulnerabilities, and deliver actionable insights that help clients strengthen their security posture. Your work will go beyond automated scans—you’ll think like an attacker, chaining vulnerabilities, developing custom tools, and executing advanced exploitation techniques. You’ll also play a key role in client communication, translating technical findings into clear business risks for both technical and executive audiences. If you’re passionate about offensive security, thrive on complex challenges, and enjoy pushing the boundaries of ethical hacking, this role is for you.
What You'll Do
- Conduct Penetration Testing – Perform web, mobile, and network penetration testing using both manual and automated techniques.
- Simulate Real-World Attacks – Execute blended and chained attack scenarios to uncover complex vulnerabilities.
- Exploit & Validate Findings – Identify, exploit, and demonstrate real-world risk to client environments.
- Develop Tools & Scripts – Create custom scripts, tools, or methodologies to enhance testing processes.
- Deliver High-Quality Reports – Produce clear, comprehensive reports for both technical and executive audiences, including remediation guidance.
- Assess Security Architecture – Evaluate systems across all layers to identify design and implementation flaws.
- Support Engagement Scoping – Assist in defining scope and approach for prospective security engagements.
- Stay Ahead of Threats – Continuously research emerging vulnerabilities, tools, and attack techniques.
Requirements
- 4–7+ years of experience in Penetration Testing and Security Assessments.
- Bachelor’s degree in Computer Science, Information Security, or related field (or equivalent experience).
- Certifications such as OSCP, OSCE, GIAC, or Pentest+ (strongly preferred).
- Proven experience across web, mobile, and network penetration testing.
- Strong knowledge of security tools (e.g., Burp Suite, Nmap, Metasploit, Wireshark, OWASP ZAP, Kali Linux, etc.).
- Experience with scripting or automation (Python, Perl, Ruby, or Bash).
- Ability to develop or modify exploits, tools, or shellcode.
- Solid understanding of networking, protocols, and application architectures.
Nice to Have
- Familiarity with reverse engineering, source code review, or malware analysis (preferred).
- Experience participating in CTFs, bug bounties, or security competitions (nice to have).
What We Offer
- 💰 USD Salary Compensation
- 🌍 100% Remote Work – Work from anywhere!
- 📈 Exciting, Diverse Projects – Work across industries and security domains.
- 🚀 Career Growth Opportunities – Expand into advanced offensive security and research.
- 🤝 Supportive & Agile Team Environment – Collaborate with experienced engineers and security professionals.
- 👊👊 Team Building Activities – Join a community that values connection and collaboration.
If you’re a Senior Penetration Tester remote ready to take on complex security challenges and make a real impact by strengthening systems from the inside out, we’d love to hear from you. Apply now and help us build more secure digital environments 🚀.
This Senior Penetration Tester remote role at Winmill Software offers a competitive salary and the opportunity to work on diverse security projects. Join a supportive team and advance your career in cybersecurity.
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