Penetration Tester 2 - AI & R&D (Remote)

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We're hiring an early-career penetration tester who already builds and tests AI, small agents, LLM apps, and model guardrails, and wants to become a deeply capable offensive-security practitioner while helping shape how modern testers work with AI.

You'll join a specialized offensive-security team working shoulder-to-shoulder with Red Team, Breach & Attack Simulation, and Bug Bounty. You'll perform real penetration testing, learn from experienced practitioners, and explore AI-augmented testing through hands-on engagement work and dedicated Friday research and development time.

We support continued growth through Hack The Box Pro Labs and role-based paths, discretionary certification funding, and a conference and training budget

What you'll do

• Execute authorized penetration tests across web applications, APIs, cloud environments, and internal networks, working under general supervision on standard assignments and seeking senior guidance on complex or novel work.
• Operate the team's agentic AI offensive tooling during real engagements to improve coverage, triage, and evidence quality. Validate whether AI-assisted results are accurate and exploitable rather than treating model output as fact.
• Help assess AI- and LLM-powered applications for direct and indirect prompt injection, jailbreaks, adversarial behavior, and related risks under senior guidance. Map testing to the OWASP Top 10 for LLM Applications, MITRE ATLAS, and NIST AI Risk Management Framework (NIST AI RMF).
• Use dedicated R&D time to reproduce emerging AI-security techniques and prototype lightweight scripts, automations, and AI-assisted testing helpers.
• Analyze findings and produce clear reports with repeatable evidence, practical reproduction steps, business impact, and actionable remediation guidance.
• Collaborate with senior testers, the Lead, and adjacent offensive-security teams; contribute improvement ideas, flag potential challenges, and grow through feedback and mentorship.

Your first 6–12 months

• Within 90 days: Complete onboarding, learn our testing practices and rules of engagement, shadow a standard test and then execute defined portions under a senior tester's general supervision, and ship a first small automation or R&D experiment.
• Within 6 months: Execute standard engagements under general supervision — escalating unfamiliar, complex, or high-risk work to senior testers — contribute to an AI-augmented testing workflow, and help assess at least one AI- or LLM-powered application.
• Within 12 months: Become a dependable contributor on standard and moderately complex tests, working under general supervision within established practices; serve as an early trusted voice on responsible AI-assisted testing; and deliver a couple of useful R&D prototypes or testing improvements.

Use your skills to make an impact
 

Why this role, and why here

This role is built for someone who learns by doing. You will get hands-on offensive work from day one, dedicated time to experiment, and a front-row seat to the evolution of AI-augmented security testing.

You will be mentored by experienced offensive-security practitioners while developing the judgment to distinguish an interesting signal from a defensible finding.

Most importantly, your work will help protect the systems and sensitive health information relied upon by millions of people.

What we're looking for

You do not need to check every box below. We welcome early-career and non-traditional applicants, including self-taught practitioners, career changers, and recent graduates whose labs, internships, open-source work, or project portfolio demonstrate what they can do.

You'll need:

A 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 demonstrated ability to execute scoped testing, validate results, and document reproducible findings across web applications, APIs, networks, or cloud environments, using labs or tools such as Burp Suite, Nmap, Metasploit, or BloodHound. Ability to write useful scripts or automations in Python or a comparable language such as PowerShell, Bash, or Ruby. Demonstrated hands-on experience building or testing small AI agents or LLM applications, plus curiosity about model guardrails, adversarial behavior, and AI-assisted offensive testing. Some exposure to security automation, DevSecOps workflows, vulnerability triage, or defensive detection work. Clear written and verbal communication, including the ability to document technical evidence, explain business impact, and collaborate through review and feedback. Eagerness to develop deep penetration-testing skills under mentorship while independently managing semi-routine work within established practices.

Certifications are a plus, not a gate. Relevant examples include CompTIA Security+, eJPT, PNPT, HTB CPTS, HTB CBBH, the HTB AI Red Teamer path, and OffSec AI Red Teamer (AI-300). Advanced credentials such as OSCP are aspirational at this level, not expected.

Strong pluses (any of these will help you stand out):

• Building or testing AI guardrails, tool-calling agents, MCP servers, or agentic observability.
• Experience with PyRIT, Garak, prompt injection testing, or AI red-teaming labs.
• CI/CD security workflows involving SAST, secret scanning, dependency or software-composition management, container scanning, CVE triage, or Docker.
• Exposure to Elastic, Splunk, another SIEM, or writing detection rules.
• Open-source contributions or a public project portfolio showing initiative, iteration, and thoughtful responses to user or community feedback.
• Experience with reconnaissance tools, OSINT, adapting offensive utilities, Hack The Box, TryHackMe, or CTF competitions.
• Participation in security communities, local meetups, online groups, or conferences such as BSides, DEF CON, or Black Hat.

How you'll work

This is a remote individual-contributor role embedded within the penetration-testing service line. You will work under general supervision, determine your approach within established practices, and seek senior guidance for genuinely new, unusually complex, or high-risk assignments.

All penetration testing is performed under authorization, within agreed scope, and according to documented rules of engagement.

You will use AI only through approved tools, data-handling practices, and acceptable-use guardrails, and you will verify AI-generated output before relying on it as evidence. The Offensive AI Engineering team builds and owns the enterprise platform; you operate and test with that platform while creating only lightweight scripts and R&D prototypes appropriate to engagement needs.

Work at Home Requirements: To ensure Home or Hybrid Home/Office employees’ ability to work effectively, the self-provided internet service of Home or Hybrid Home/Office employees must meet the following criteria: At minimum, a download speed of 25 Mbps and an upload speed of 10 Mbps is required; wireless, wired cable or DSL connection is suggested. In certain roles, the minimum recommended internet speed required by Humana may not be sufficient for business needs. Humana reserves the right to require associates to upgrade their internet service if necessary. Work from a dedicated space lacking ongoing interruptions to protect member PHI / HIPAA information.

 

Travel: While this is a remote position, occasional travel to Humana's offices for training or meetings may be required.

 

Scheduled Weekly Hours

40

Pay Range

The compensation range below reflects a good faith estimate of starting base pay for full time (40 hours per week) employment at the time of posting. The pay range may be higher or lower based on geographic location and individual pay will vary based on demonstrated job related skills, knowledge, experience, education, certifications, etc.

 

$97,900 - $133,500 per year

 

This job is eligible for a bonus incentive plan. This incentive opportunity is based upon company and/or individual performance.

Description of Benefits

Humana, Inc. and its affiliated subsidiaries (collectively, “Humana”) offers competitive benefits that support whole-person well-being. Associate benefits are designed to encourage personal wellness and smart healthcare decisions for you and your family while also knowing your life extends outside of work. Among our benefits, Humana provides medical, dental and vision benefits, 401(k) retirement savings plan, time off (including paid time off, company and personal holidays, paid parental and caregiver leave), short-term and long-term disability, life insurance and many other opportunities.

Application Deadline: 10-16-2026
About us
 About Humana: Humana Inc. (NYSE: HUM) is a leading U.S. healthcare company. Through our Humana insurance services and our CenterWell healthcare services, we make it easier for the millions of people we serve to achieve their best health – delivering the care and service they need, when they need it. These efforts are leading to a better quality of life for people with Medicare and Medicaid, families, individuals, military service personnel, and communities at large. Learn more about what we offer at Humana.com and at CenterWell.com.

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Equal Opportunity Employer

It is the policy of Humana not to discriminate against any employee or applicant for employment because of race, color, religion, sex, sexual orientation, gender identity, national origin, age, marital status, genetic information, disability or protected veteran status. It is also the policy of Humana to take affirmative action, in compliance with Section 503 of the Rehabilitation Act and VEVRAA, to employ and to advance in employment individuals with disability or protected veteran status, and to base all employment decisions only on valid job requirements. This policy shall apply to all employment actions, including but not limited to recruitment, hiring, upgrading, promotion, transfer, demotion, layoff, recall, termination, rates of pay or other forms of compensation and selection for training, including apprenticeship, at all levels of employment.