Principal Penetration Tester

Clearwater; United States; On-site; USD 120,000 - 150,000; Full time

Job summary

Clearwater is seeking an experienced offensive security professional to deliver testing across network, cloud, mobile, web, AI, and wireless domains. You will work with clients, project management, and engagement leaders to shape approaches and proposals.

Role includes developing best practices, templates, and training materials, mentoring junior testers, and maintaining high client satisfaction. Expect a base salary in the six-figure range with strong benefits and a flexible work environment.

Qualifications

• 5–10 years delivering offensive security services in multiple domains.
• Certifications preferred: OSCP, OSEP, CRTO, GWAPT, CRTL.
• Strong written communication and client reporting skills.

Responsibilities

• Deliver offensive security services across networks, cloud, mobile, web, and AI.
• Collaborate with clients, PMs, and engagement leaders to develop proposals.
• Develop best practices, methodologies, and templates for the team.
• Achieve high client satisfaction and meet expectations.
• Mentor junior testers and supervise billable work.

Skills

Offensive security

Penetration testing

Client engagement

Mentoring

Team leadership

Security tooling knowledge

Tools

Nessus

Burp Suite

Wireshark

Kali Linux

Job description

• Deliver offensive security services in the following areas including network, cloud, mobile application, web application, and artificial intelligence (AI) and wireless penetration testing and related technical security assessments.
• Collaborate with clients, project management, and engagement leaders to identify, develop, and obtain information for developing approach proposals.
• Assist in the development of best practices, strategies, methodologies, and documentation/templates for use by the penetration testing team.
• Achieve high levels of client satisfaction on all engagements by meeting or exceeding client expectations set by engagement leaders and project managers.
• Provide thought leadership through the delivery of webinars, participation in industry groups and authoring technical blog articles and case studies.
• Work in collaboration with penetration testing leadership to continue to update and mature capabilities.
• Mentor and develop junior penetration testers, advancing their consulting skills, tradecraft, and technical knowledge.
• Billable hours target: 1664 hours annually (equivalent to 80 % utilization)

Specific Job Responsibilities

• Deliver offensive security services in the following areas including network, cloud, mobile application, web application, and artificial intelligence (AI) and wireless penetration testing and related technical security assessments.
• Collaborate with clients, project management, and engagement leaders to identify, develop, and obtain information for developing approach proposals.
• Assist in the development of best practices, strategies, methodologies, and documentation/templates for use by the penetration testing team.
• Achieve high levels of client satisfaction on all engagements by meeting or exceeding client expectations set by engagement leaders and project managers.
• Provide thought leadership through the delivery of webinars, participation in industry groups and authoring technical blog articles and case studies.
• Work in collaboration with penetration testing leadership to continue to update and mature capabilities.
• Mentor and develop junior penetration testers, advancing their consulting skills, tradecraft, and technical knowledge.
• Billable hours target: 1664 hours annually (equivalent to 80 % utilization)

Requirements

EXPERIENCE REQUIRED

• 5-10 years’ experience delivering offensive security services in at least two of the following areas, including network, cloud, mobile application, web application, and/or artificial intelligence (AI) penetration testing and related technical security assessments.

Qualifications, Skills, & Knowledge

• Certifications preferred: OSCP, OSEP, CRTO, GWAPT, CRTL
• Knowledge of proprietary and open-source technical security testing tool suites (e.g., Nessus, Burp Suite, Wireshark, Kali Linux, etc.).
• Demonstratable analytic and problem-solving skills, especially with technical securityanalysis and client reporting.
• Ability to work without supervision on a variety of projects simultaneously and exercising good judgment and initiative to manage priorities.
• Strong written communication skills translating technical testing results into findings, observations, and recommendations for possible client remediation.
• Experience mentoring junior penetration testers and/or team members to help them advance.
• Ability and willingness to learn about creating and executing repeatable work processes and procedures and learning techniques for planning, developing materials, and delivering training on technical subject matter and software products.
• Ability to embrace Clearwater’s CLEAR core values (Commitment to Client Success, Lead with Accountability, Integrity & Collaboration, Excellence in All That We Do, Advance Colleague Success, Respect & Transparency) and culture.

The base salary range for this role is $120,000- 150,000. Base salary is part of our total rewards package which also includes the opportunity for merit-based salary increases, eligibility for our 401(k) plan, medical, dental, vision, life and disability insurances and leaves provided in line with your work state. Our robust time-off policy includes flexible paid time off, 11 paid holidays, and paid sick time. Total compensation, including base salary to be offered, will depend on elements unique to each candidate, including applicable candidate experience, skills, education and other factors permitted by law.

Disclaimer: The above statements are intended to describe the general nature and level of work being performed by people assigned to this position. They are not to be construed as an exhaustive list of all responsibilities, duties, and skills required of colleagues in the role. All colleagues may be required to perform duties outside of their normal responsibilities from time to time, as needed.

Clearwater is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. Please inform Clearwater/Redspin’s Recruiting team if you need any assistance completing any forms or to otherwise participating in the application process.

Mental/Physical Requirements: Fast paced environment handling multiple demands. Must be able to exercise appropriate judgment as necessary. Requires a high level of initiative and independence. Excellent written and oral communication skills required. Requires the ability to use a personal computer for extended periods of time.

Disclaimer: The above statements are intended to describe the general nature and level of work being performed by people assigned to this position. They are not to be construed as an exhaustive list of all responsibilities, duties, and skills required of colleagues in the role. All colleagues may be required to perform duties outside of their normal responsibilities from time to time, as needed.

Clearwater is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. Please inform Clearwater/Redspin’s Recruiting team if you need any assistance completing any forms or to otherwise participating in the application process.

Mental/Physical Requirements: Fast paced environment handling multiple demands. Must be able to exercise appropriate judgment as necessary. Requires a high level of initiative and independence. Excellent written and oral communication skills required. Requires the ability to use a personal computer for extended periods of time.