Job Details

Senior Penetration Tester

Waterleaf International is seeking a self-starting, highly motivated Sr. PenTester professional to join our CyberleafTM Cybersecurity-as-a-Service (CSaaS, Engineering and Sales organization as the Senior Penetration Testing Engineer. A qualified candidate will have the abilities to:  Plan, communicate, coordinate, and conduct red team activities, penetration tests, and security assessments for applications, systems, including ICS-OT and enterprise networks while adhering to strict rules of engagement and ethical cyber operational behavior. 

You Are Flexible and Ready For Anything 

  • The cybersecurity industry is rapidly changing, and we build products that evolve to protect our customers from the latest threats. We pride ourselves on being one step ahead of attackers and preparing for what’s to come. 

  • You are comfortable in a start-up environment and a self-starter. 


  • Develop attack scenarios and campaigns to meet customer objectives, requirements and provide a well-balanced challenge to the defenders. 

  • Configure and deploy network appliances/internal tools for testing. 

  • Manage wireless RF testing – WiFi and other wireless communication networks 

  • ICS-OT, IIOT and connected vehicle testing 

  • Strategize, coordinate, and provide guidance to all Red Team operators to deconflict attack scenarios and achieve all collective objectives. 

  • Rehearse attack scenarios and use of tools prior to engagements to ensure a sufficient level of success 

  • Perform information technology security research to remain current on emerging technology trends and develop exploits for disclosed and undisclosed vulnerabilities 

  • Define and maintain Red Team standard operating procedures. 

  • Perform security reviews of application designs, source code, and deployments as required, covering all types of applications (web application, web services, mobile applications, thick applications, SaaS) 

Qualifications (Minimum) 

  • 5+ years of experience in Red Team Operator roles and vulnerability assessments 

  • Developing, extending, or modifying exploits, shellcode or exploit tools 

  • ICS-OT testing of government and enterprise networks and hardware 

  • Experience with utilizing penetration testing framework such as MITRE ATT&CK & OWASP 

  • Experience with Nmap, Burp Suite, PowerShell, C#, Ghost Pack, Bloodhound, Cobalt Strike, Kali Linux, Metasploit 

  • 5+ years wireless pentesting experience with Aircrack, Airsnort, Kismet and others. 

Requirements/Certifications/Licenses : 

  • Bachelors degree or higher  

  • 5+ years’ penetration testing experience as well as additional experience in network security, reverse engineering, programming, databases, web applications 

  • One or more of the following certifications preferred: 

  1. Offensive Security Certified Professional (OSCP) 

  1. Certified Ethical Hacker (CEH) Certification 

  1. GIAC Penetration Tester (GPEN) Certification 

Qualifications (Preferred): 

  • 7+ years direct or equivalent experience in areas of manual penetration testing (web application, host, network, wireless, mobile, cloud), exploit development, fuzzing, and designing countermeasures to identified security vulnerabilities/risks. 

  • Knowledge of attack surfaces in cloud, web technologies, networks, modern applications. (microservices/containers), and operating systems; should demonstrate the ability to analyze closed source applications using several off-the-shelf or custom developed tools. 

  • Experience with red team tools and infrastructure, including deployment, maintenance, and use of multiple C2 frameworks. 

  • Experience evading host and network-based security systems (e.g., WAFs, anti-phishing, AV/EDR, behavioral analysis). 

  • Proficient in relevant programming and scripting languages such as shell, Python, and Ruby, with the ability to develop custom scripts, exploits, and tools to support penetration testing. Conversant in multiple others such as PowerShell, Perl, C/C++, C#, Java, or assembly, sufficient to read and modify existing code. 

  • Excellent and professional communication skills (written and verbal) with an ability to articulate complex topics in a clear and concise manner. 

  • Ability to scope, price and evaluate engagements – time and resource estimates. 


  • Experience with user- and kernel-mode debuggers on Windows and/or Linux. 

  • Experience password cracking for common operating systems and applications. 

  • Published or presented security research, security advisories, and/or open-source security tools. 

  • Experience identifying security issues through code review. 

  • Reverse Engineering / Malware analysis. 

  • Ability to leverage past web application and API development experience for web app penetration testing and secure design advice for customer development teams. 

  • Experience with a range of engagement types - red team, purple team, stealth, unaided (“black box”), aided (“white box”) - of varied targets - external, internal, cloud infrastructure, embedded devices, etc. 

  • Ability to teach/instruct and lead junior team members as they develop. 

  • Threat hunting and knowledge of SIEM/SOAR and SOC operations. 

Desired Experience/Capabilities: 

  • Connected vehicle and Intelligent Transportation System testing (ITS) experience is desired 

  • Government/Municipality testing of ICS-OT networks 

Preferred Fields of Study: 
Computer and Information Science, Information Technology, Computer Applications, Computer Engineering, Information Cybersecurity, Network Engineering. 

Certification(s) Preferred: 
Offensive Security Certified Expert (OSCE), Offensive Security Certified Professional (OSCP), Burp Suite Certified Practitioner, GIAC Penetration Tester (GPEN), GIAC Exploit Researcher and Advanced Penetration Tester (GXPN), Certified as GIAC Web Application Penetration Tester (GWAPT). 

We are a rapidly growing telecommunications and cybersecurity company working in the defense and commercial enterprise space. Private Equity backed, we are at an inflection point and are experiencing significant growth. Based in SW Florida and with offices in Atlanta and Wichita both work at home or FL locations are acceptable.  

We are innovative, creative, and mission-focused with services and products that are delivering a disruptive business model and technologies to the global cybersecurity market. The culture is one of innovation, openness, communication, honesty, and integrity. We have fun and enjoy what we do, are at times irreverent and always focused on deliverables, customer satisfaction and shareholder returns.  

Due to potential Federal contract requirements, applicants must be US citizens. And must be able to obtain and hold a SECRET or TS Clearance. 

Our clients are varied and include government, DIB as well as enterprise that value security and skilled security practitioners. We research and publish vulnerabilities, participate in industry research and run our own labs. 

Our team is varied and lives throughout the US with HQ in SW FL and offices in Atlanta and MD/DC. We primarily work remote and do have lab, testing and staging areas as well. 

We have highly competitive benefits with a package that includes paid time off, platinum health insurance, dental and vision coverage, maternity/paternity leave, 401K w/employer contribution, education, flex schedules and time shifting, support for your passion projects and opportunities for professional growth. 

Job Type: Full-time (will consider contract employment but no recruiters) 

Compensation: We pay for performance, capabilities and skills…we are SME’s and expect you to be as well. 

Base Pay: Competitive based on qualifications 

Bonuses: Team and individual bonuses based on Company/Team success  

Employee Stock Options – we are a private company, and all employees get ESO’s


  • 401(k) matching 

Dental insurance 

  • Flexible schedule 

  • Health insurance 

  • Paid time off 

  • Professional development assistance 

Vision insurance 

  • Maternity/Paternity Leave 

  • Home office stipend 

Senior Level
$85,000.00 - $150,000.00