Cybersecurity Penetration Tester

Cybersecurity Penetration Tester

Reports to: Cybersecurity Operations Manager

Status: Regular, Full-Time, Exempt

Location: Remote, USA

POSITION SUMMARY

As Penetration Tester at FIT Cybersecurity, your responsibilities would include testing client’s internal and external networks, web applications, and APIs. The Penetration Tester will provide debriefing to both client technical and executive teams on security assessment findings. As a consultant, you'll solve challenging technical problems and build creative solutions. As a trusted advisor, you'll provide your expert opinion to help our clients navigate difficult business decisions. And as a security associate, you'll lead teams on one-of-a-kind engagements, mentor co-workers, and contribute significantly to the advancement of our assessment and penetration testing practice.

ABOUT FIT SOLUTIONS

FIT Solutions is an innovative national IT and Cybersecurity Services firm, and we are growing every day. We are focused on creating a culture of elite raving fans for our employees that solves business problems for our clients. We are on a mission to impact the lives touched by technology. We teach and promote individuals to set and achieve their personal, professional, and financial goals through the work we do together. Measuring results against best-in-class businesses, we are focused on hitting targets. We are a humble and adaptable group of people who continue to train, and role play daily in pursuit of our goals. We are a great fit for team members that are aligned and thrive in a fast-paced, results driven environment.

PRIMARY OBJECTIVES

• Identify and disclose vulnerabilities and vulnerable components of a client infrastructure.
  
• Execute webapp and network pen tests independently, providing clients the remediation guidance for all significant identified vulnerabilities.
• Contribute to Assessment Research and Development initiatives (identifying new 0-day vulnerabilities, improving attack methodologies, improving penetration test tolling, etc.).
• Develop and adhere to process documentation in support of cyber penetration testing execution.
  

SECONDARY OBJECTIVES

• Identify emerging security risks and collaborate with internal service teams and clients to develop appropriate mitigation strategies.
• Configure and support various operating systems (Windows, Linux, UNIX, macOS), virtualization platforms (VMware, Xen, Hyper-V), and cloud environments (AWS, Azure) used in penetration testing.
• Effectively assess and communicate security risks, business impact, and appropriate levels of urgency to stakeholders.
• Lead client engagement kickoff meetings, technical debriefings, and executive presentations.
• Collaborate effectively with internal teams, external organizations, and client stakeholders throughout security assessment engagements.
• Share knowledge, provide technical guidance, and train team members on penetration testing methodologies, tools, and best practices.
• Support continuous improvement initiatives to enhance the effectiveness and efficiency of penetration testing services.
• Perform other duties as assigned.
  

COMPETENCIES

• Excellent organizational, verbal, and written communication skills, including the ability to explain complex technical findings to nontechnical audiences.
• Strong understanding of cybersecurity fundamentals, common vulnerabilities, attack methodologies, and remediation strategies.
• Demonstrated experience in vulnerability discovery, security engineering, application security, and penetration testing.
• Intermediate to advanced proficiency with virtualization and containerization technologies.
• Strong analytical, critical-thinking, and problem-solving skills.
• Ability to independently manage multiple client engagements, prioritize competing deadlines, and deliver high-quality results.
• Strong attention to detail, particularly in documenting vulnerabilities, supporting evidence, and remediation recommendations.
• Ability to work collaboratively in a remote, client-focused consulting environment.

EDUCATION AND EXPERIENCE

• Required Certification: GIAC Penetration Tester (GPEN).
• Preferred Certification: Offensive Security Certified Professional (OSCP). Additional advanced cybersecurity certifications, including OSCE, GWAPT, GXPN, or CISSP, are a plus.
• Required Work Sample: Candidates must be able to provide a sanitized sample penetration testing report demonstrating their ability to document vulnerabilities, assess risk, present technical findings, and communicate actionable remediation recommendations. All samples must exclude confidential client information.
• Strong foundational knowledge and hands-on experience in web application and network penetration testing. Experience with mobile applications, APIs, cloud environments, and hands-on cybersecurity training platforms such as HackTheBox and TryHackMe is a plus.
• Previous experience in cybersecurity consulting, penetration testing, or offensive security assessments.
• Solid understanding of common web application vulnerabilities, exploitation techniques, and remediation options.
• Knowledge of IT infrastructure, security engineering, system and network security, authentication protocols, and applied cryptography.
• Experience with configuration management, system maintenance, integration testing, penetration testing, and vulnerability analysis.
• Knowledge of system architectures and networking technologies, including client/server environments, web hosting, directory services, firewalls, WAN, MAN, LAN, switches, and routers.
• Proficiency with macOS, Linux, and Windows operating systems.
• Experience preparing professional penetration testing reports and presenting assessment results to clients.
• Familiarity with industry-standard penetration testing methodologies, frameworks, and tools.

WORK ENVIRONMENT AND TRAVEL

• Remote position with occasional travel required for client engagements, meetings, or other business needs.
• Must be able to work independently and collaborate effectively with geographically distributed teams.
• Occasional testing outside of regular business hours, including evenings and weekends, may be required based on client needs and engagement requirements.
  

BENEFITS

FIT Solutions has your back, and is proud to offer a rich benefit package to our employees, including:

• Health, Dental & Vision Insurance (premiums paid up to 99% for employee coverage)
  • Options include, PPO, HDHP, HMO and ACO
  • Multiple carrier options
• FSA (dependent and medical), HSA options (for qualified plans) and supplemental insurance options
• $10,000 employer-paid Life Insurance & AD&D (employees have the option to buy up)
• Paid holidays
• Paid time off
• Paid sick leave
• Flexible “hybrid” work environment
• Retirement plan (401K)
• Professional training & development opportunities

This position may occasionally require testing outside of regular business hours, including weekends.

PHYSICAL REQUIREMENTS

• Ability to spend prolonged periods of time standing, speaking, walking, driving, and/or sitting
  
• Requires ability to occasionally lift up to 25lbs
  
• Position may require travel: Up to 5%
  
• Reasonable accommodation may be made to enable individuals with disabilities to perform the essential requirements.
  

AAP/EEO Statement
FIT Solutions is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. We are committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. We will not tolerate discrimination or harassment based on any of these characteristics