Senior Cloud Security Penetration Tester- Remote (Anywhere in the U.S.)

GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation’s top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.

About the Role

We are seeking a highly skilled Senior Cloud Security Penetration Tester with strong AWS expertise to join our Threat & Attack Simulation team. In this role, you will lead cloud penetration testing engagements, focusing on network penetration testing and assumed breach scenarios to validate real-world risks in cloud environments. You will work as part of a supportive 3-person project structure, serving as either the lead consultant (primary performer) or providing technical oversight, depending on the engagement. The ideal candidate will combine technical excellence with outstanding communication skills and demonstrate initiative in driving security improvement efforts.

Key Responsibilities

• Lead cloud penetration testing engagements with a focus on AWS environments
• Perform network penetration testing and assumed breach scenarios to validate security risks
• Execute real-world attack simulations to demonstrate the impact of cloud misconfigurations
• Develop and implement sophisticated testing methodologies for cloud environments using tools like ScoutSuite, Prowler, CloudMapper, and Pacu
• Author comprehensive client deliverables including executive summaries, detailed technical reports, and remediation recommendations
• Present findings and recommendations to technical and non-technical stakeholders
• Stay current with emerging cloud security threats, attack vectors, and defensive strategies
• Collaborate with internal teams and peers to continually improve testing methodologies and tooling

Required Qualifications

• 3-5 years of experience in cloud security penetration testing, with strong emphasis on AWS environments
• Demonstrated expertise in network penetration testing and assumed breach methodologies
• In-depth understanding of cloud architecture, security controls, and attack vectors
• Experience with cloud-specific security testing tools (ScoutSuite, Prowler, CloudMapper, Pacu)
• Experience in writing clear, actionable security reports for both technical and executive audiences
• Excellent verbal communication skills for client presentations and stakeholder interactions
• Strong initiative and self-direction, with ability to lead complex security engagements
• OSCP certification or equivalent demonstrable penetration testing experience

Preferred Qualifications

• AWS security certifications (AWS Certified Security - Specialty, etc.)
• Experience with multi-cloud environments (AWS, Azure, GCP)
• Knowledge of containerization technologies and serverless security testing
• Familiarity with compliance frameworks (SOC2, PCI-DSS, HIPAA, etc.)
• Familiarity with LLM/Agentic tools to improve efficiency
• Experience developing custom tools or scripts for cloud security testing
• Background in red teaming or adversary simulation

What We Offer

• 100% remote work with minimal travel requirements
• Opportunity to work with diverse, high-profile clients including Fortune 500 companies and government agencies
• Opportunity to lead high-impact security engagements across various industries
• Collaborative environment working alongside cloud security experts within our Threat & Attack Simulation team
• Clear progression opportunities serving as both lead consultant and technical oversight roles
• Continuous learning and professional development opportunities

Team Structure

You'll report to a team lead and work within our proven 3-person engagement model that includes a lead consultant (primary performer), technical oversight consultant, and managing consultant for escalation support. This structure ensures quality delivery while providing mentorship opportunities and collaborative problem-solving.

This role requires a dynamic security professional who can independently drive engagements while delivering exceptional client value through practical, real-world security testing and clear communication of findings.

We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.

Why GuidePoint?

GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1000 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 4,200 customers.

Firmly-defined core values drive all aspects of the business, which have been paramount to the company’s success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.  

This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.

Some added perks….

• Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
• Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family) and GPS will contribute in one lump sum: ($500 per EE annually / $1000 per family annually (includes spouse/children/family options)
• Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
• 12 corporate holidays and a Flexible Time Off (FTO) program
• Healthy mobile phone and home internet allowance
• Eligibility for retirement plan after 2 months at open enrollment
• Pet Benefit Option