Penetration Tester 2 – AI, R&D

Humana

. Execute authorized penetration tests across web applications, APIs, cloud environments, and internal networks .

Posted 10/13/2026full-timeRemote • United StatesJunior💰 $97,900 - $133,500 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in executing penetration tests across web applications, APIs, and cloud environments, with a strong focus on AI-assisted security techniques and automation. Proficient in documenting findings and collaborating effectively within security teams to enhance overall security posture.

Highest-signal resume keywords

Penetration TestingAI-Assisted Security TechniquesScripting in PythonExperience with Burp SuiteVulnerability Triage

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Penetration TestingScripting in PythonScripting in PowerShellScripting in BashScripting in RubyVulnerability TriageAI Security TechniquesWeb Application SecurityAPI SecurityCloud Security

Soft Skills

Clear CommunicationCollaborationCuriosityDocumentation SkillsAbility to Manage Work Independently

Tools & Technologies

Burp SuiteNmapMetasploitBloodHoundDockerElasticSplunkSIEMCI/CD Security WorkflowsDevSecOps

Certifications & Qualifications

CompTIA Security+EJPTPNPTHTB CPTSHTB CBBHHTB AI Red Teamer PathOffSec AI Red Teamer (AI-300)

Industry Keywords

OWASP Top 10MITRE ATLASNIST AI RMFAdversarial BehaviorPrompt Injection TestingAgentic AISecurity AutomationOpen-Source ContributionsCTFsSecurity Communities

Tech Stack

Tools & technologies

CloudCyber SecurityDockerPythonRubySplunk

About the role

Key responsibilities & impact

Execute authorized penetration tests across web applications, APIs, cloud environments, and internal networks
Operate agentic AI offensive tooling during engagements to improve coverage, triage, and evidence quality
Validate AI-assisted results for accuracy and exploitability
Assess AI- and LLM-powered applications for prompt injection, jailbreaks, adversarial behavior, and related risks
Map testing to OWASP Top 10 for LLM Applications, MITRE ATLAS, and NIST AI RMF
Reproduce emerging AI-security techniques during dedicated R&D time
Prototype lightweight scripts, automations, and AI-assisted testing helpers
Analyze findings and produce reports with evidence, reproduction steps, business impact, and remediation guidance
Collaborate with senior testers, the Lead, Red Team, Breach & Attack Simulation, and Bug Bounty teams
Complete onboarding, shadow standard tests, execute defined portions under supervision, and deliver automation or R&D experiments
Progress toward independently executing standard and moderately complex engagements under general supervision
Work within authorization, agreed scope, documented rules of engagement, approved AI tools, and data-handling guardrails

Requirements

What you’ll need

Bachelor's degree in computer science, cybersecurity, or a related field and roughly 1–2+ years of related experience, or equivalent demonstrated hands-on capability through internships, labs, CTFs, open-source work, or a strong project portfolio
Working offensive-security knowledge and ability to execute scoped testing, validate results, and document reproducible findings across web applications, APIs, networks, or cloud environments
Experience with Burp Suite, Nmap, Metasploit, or BloodHound
Ability to write scripts or automations in Python, PowerShell, Bash, or Ruby
Hands-on experience building or testing small AI agents or LLM applications
Curiosity about model guardrails, adversarial behavior, and AI-assisted offensive testing
Exposure to security automation, DevSecOps workflows, vulnerability triage, or defensive detection work
Clear written and verbal communication and ability to document technical evidence, explain business impact, and collaborate through review and feedback
Ability to independently manage semi-routine work within established practices and seek senior guidance for complex or high-risk assignments
Certifications are a plus, including CompTIA Security+, eJPT, PNPT, HTB CPTS, HTB CBBH, HTB AI Red Teamer path, or OffSec AI Red Teamer (AI-300)
Strong pluses include AI guardrails, tool-calling agents, MCP servers, agentic observability, PyRIT, Garak, prompt injection testing, AI red-teaming labs, CI/CD security workflows, SAST, secret scanning, dependency or software-composition management, container scanning, CVE triage, Docker, Elastic, Splunk, SIEM, detection rules, open-source contributions, OSINT, Hack The Box, TryHackMe, CTFs, security communities, meetups, or security conferences
Minimum home internet speed of 25 Mbps download and 10 Mbps upload
Dedicated workspace without ongoing interruptions to protect member PHI/HIPAA information

Benefits

Comp & perks

Hack The Box Pro Labs and role-based paths
Discretionary certification funding
Conference and training budget
Mentorship and feedback from experienced offensive-security practitioners
Medical, dental, and vision benefits
401(k) retirement savings plan
Paid time off
Company and personal holidays
Paid parental and caregiver leave
Short-term and long-term disability
Life insurance
Bonus incentive plan based on company and/or individual performance
Remote work arrangement
Dedicated Friday research and development time