Full-Time

Senior Penetration Tester

Threat & Attack Simulation

Posted on 8/26/2025

GuidePoint Security

GuidePoint Security

1,001-5,000 employees

Cybersecurity consulting, software solutions, managed services

No salary listed

Remote in USA

Remote

U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions.

Category
DevOps & Infrastructure (2)
,
Required Skills
AWS
Requirements
  • 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
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
Desired 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

GuidePoint Security helps organizations assess and reduce cybersecurity risk through a mix of security technologies, consulting, and managed security services for enterprise and government clients. It works by assessing a client’s security posture, recommending and deploying appropriate tools and controls, and continuously monitoring and managing security operations to detect and respond to threats. The company differentiates itself with deep industry knowledge and hands-on practitioner experience from the DoD, Intelligence Communities, and Fortune 500, enabling tailored solutions for complex, mission-critical needs instead of generic products. Its goal is to help clients make informed security decisions, lower risk exposure, and defend against evolving cyber threats using a combination of technology, expertise, and managed services.

Company Size

1,001-5,000

Company Stage

Growth Equity (Non-Venture Capital)

Total Funding

N/A

Headquarters

Reston, Virginia

Founded

2011

Simplify Jobs

Simplify's Take

What believers are saying

  • Red Sift partnership brings email security to enterprise customers expanding reseller lineup.
  • CNAPP Enablement Service streamlines cloud-native security for large organizations.
  • Veza integration strengthens identity security with proactive risk management insights.

What critics are saying

  • Mandiant erodes market share with superior AI-powered MDR in 12-18 months.
  • CrowdStrike Falcon causes client attrition via advanced automation in 6-12 months.
  • AWS Bedrock Guardrails commoditizes AI governance undercutting reseller demand in 6-12 months.

What makes GuidePoint Security unique

  • GuidePoint aligns AI Readiness Assessments with NIST AI RMF's Map, Measure, Manage, Govern functions.
  • Tailored Regulatory Compliance Strategy navigates EU AI Act's global standards for clients.
  • Ed's red team expertise oversees generative AI implementations enhancing cybersecurity.

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Benefits

Health Insurance

Dental Insurance

Paid Holidays

Unlimited Paid Time Off

Remote Work Options

Phone/Internet Stipend

401(k) Retirement Plan

Pet Insurance

Company News

FAIR Institute
Dec 9th, 2025
Four Findings from FAIRCON25

Four findings from FAIRCON25. I had the fun, engaging, energizing, and informative pleasure of attending the 10th Annual FAIR Conference in New York City this year with its team from GuidePoint Security. This blog post is contributed by GuidePoint Security, a FAIR Institute sponsor. Author Ben Moreland is Risk Practice Director at GuidePoint Security The cyber risk management community there was great, breakout sessions were packed with lessons learned, and the sessions, education, and content were extremely engaging. I took away more than four findings, but I couldn't resist the consonance of this catchy title. Here are four findings (or key takeaways) that resonated with me: * How you COMMUNICATE risk is as important as how you MEASURE risk. Jack Jones and the FAIR community have given scientific and mathematical rigor to risk modeling and analysis. But that doesn't mean you need to be a mathematician to know, understand, and communicate cyber risk. Using the FAIR model provides measurable, data-driven analysis that enables decision making. Being able to communicate risk in dollars and probabilities is one of many frequencies that may resonate with your board or audit committee. Traditional qualitative "measures" and stoplight colors provide an at-a-glance understanding of risk; but having measured, accurate, risk ranges with impact and probability add significantly more confidence to the executive team for conversations around information and cybersecurity investments, trade-offs, and prioritization. * Risk decision intelligence is a force multiplier Reframing "Cyber Risk Quantification" to "Cyber Decision Intelligence" was a challenge posed to conference attendees by Saket Modi, CEO of SAFE. Thinking of it another way, cyber risk quantification is the action, but decision intelligence is the outcome. The late, great, venerated General Colin Powell was quoted with "Perpetual optimism is a force multiplier". I'm a huge fan of Colin Powell and would like to borrow from him in stating "risk decision intelligence is (also) a force multiplier". When I led Information Security for a media company I was often asked by peers and other executives: "Are we secure?". As simple and generic as that statement is - they were serious. And as CEOs, CIOs, CFOs, and other executives rely on big data and business intelligence to amplify their ability to make decisions that drive and grow their business, so, too, should CISOs and other cyber executives. * Compliance is your floor, not your ceiling "Compliance is your floor, not your ceiling", are words I've heard Alla Valente, Principal Analyst at Forrester, utter before, but at FAIRCON, they hit a nerve. Compliance is important - AND - you don't have to stop there. At GuidePoint Security, FAIR Institute Inc. help manage and treat risk for so many customers. In contrast, I've seen too many organizations limit their IT+information+cyber-security programs to meet compliance requirements and audit standards. Sometimes a shiny new tool or popular platform that vendors are marketing and CISOs are raving about get added to the security stack too. But, as FAIR Institute Inc. know, being compliant and having cool security tools doesn't make your organization and data "secure". While 100% cyber risk elimination isn't possible in today's digital age, compliance with regulations and standards linked to SOX, PCI, CMMC, HIPAA, NIST and others is only the beginning, a catalyst. Governance, Risk and Compliance (GRC) leaders need to correlate risks in the context of business strategies. Cyber risk quantification or - to use a new and emerging term - cyber business intelligence - aims to do just that. So I encourage GRC leaders, risk managers, cyber executives to evolve their programs beyond compliance if they're not doing so already. * Quantifying cyber risk is a journey, FAIR Institute Inc. is all at different stages FAIR Institute Founder, Nick Sanna, opened the FAIRCON25 welcome address with "The Future of Cyber Risk Management Starts Here." As I met with, spoke with, and listened to attendees, I really understood the journey FAIR Institute Inc. is on together. Students I met from Georgetown University and Harvard are learning fundamentals and frameworks around cyber risk management. Several risk managers I spoke with or heard from identified pain points and lessons learned in moving qualitative third-party risk management to a more continuous, autonomous, quantitative risk-aligned program. Executive speakers demonstrated a variety of ways risk may be communicated and reported. Each offered valuable insights into risk management stages. The best part of the conference for me was knowing I'm on the journey with a like-minded community all focused on a similar mission to improve cyber risk management. Learn more about quantifying your cyber risk.

ChannelE2E
Sep 15th, 2025
Red Sift Joins GuidePoint Security's Lineup of Reseller Offerings

Red Sift has partnered with GuidePoint Security in a new reseller partnership that brings Red Sift's email security and attack surface management platform to GuidePoint's enterprise customers.

GuidePoint Security
Jul 21st, 2025
GuidePoint Security Launches New Cyber Risk Quantification Service To Help Organizations Make Smarter Security Investments

GuidePoint Security launches new Cyber Risk Quantification Service to help organizations make smarter security investments.

ADD-USA, Inc.
Jun 17th, 2025
GitGuardian Partners with GuidePoint Security to Strengthen Application Security Offerings

GitGuardian partners with GuidePoint Security to strengthen application security offerings.

Cyber Technology Insights
May 21st, 2025
Bitwarden Now Offered Through GuidePoint Security

Bitwarden, the trusted leader in password, passkey, and secrets management, announced a strategic reseller partnership with GuidePoint Security, a leading cybersecurity solutions provider.

INACTIVE