Freelance Offensive Security Engineer Jobs in Indiana

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We're hiring the technical leader of our red team, a hands-on Lead who runs our hardest adversary-emulation campaigns, sets how the team operates, owns the rules of engagement, and moves us into AI-augmented red teaming. You will own the craft: the tradecraft, the standards, the objective-based operations, and the safe, authorized conduct of offensive work.

Red teaming here is not vulnerability coverage and not automated control validation, it's objective-based adversary emulation: we measure whether the enterprise can detect, resist, and respond to a realistic adversary pursuing a mission objective, across network, social engineering, physical, and assumed-breach domains, mapped to MITRE ATT&CK and validated with our defenders through purple teaming.

This is a remote role on a specialized offensive-security team, red teaming shoulder-to-shoulder with Penetration Testing, Breach & Attack Simulation, and Bug Bounty. Fridays are for research and development. You'll have Hack The Box Pro Labs and role-based paths, discretionary certification funding, and a conference/training budget.

What you'll own

• The red-team tradecraft and standards. You set the methods, playbooks, and quality bar the team operates to. These are adversary emulation, C2 tradecraft, initial access, privilege escalation, lateral movement, defense evasion, and assumed-breach methodology - and keep them current as adversaries and defenses evolve.

• The hardest campaigns. You scope, lead, and land the most complex objective-based operations end-to-end, and you're the technical escalation point when an operation hits a wall.

• Rules of engagement and safe conduct. You own the authorization, scoping, deconfliction, and rules-of-engagement governance that keep offensive operations legal, in-scope, and safe.

• AI-augmented red teaming, on two fronts. You drive how the team operates and matures agentic AI offensive tooling to sharpen planning, tradecraft research, evidence synthesis, reporting, and you lead adversarial testing of the enterprise's own production AI systems as targets.

• Defensive impact and functional influence. You turn campaigns into executive-consumable risk narratives, advise leadership on the direction of the red-team function, and partner with detection engineering and the SOC to close the loop on what we found.

What you'll do

• Set and govern the team's adversary-emulation methodology, C2 tradecraft standards, and evidence-quality bar; standardize how objective-based operations are scoped, executed, and reported.

• Lead the most complex red-team campaigns, external/internal network, social engineering, assumed-breach, and full-scope objective operations, with full autonomy, and mentor Senior red teamers on tradecraft without being their manager.

• Own rules of engagement: define authorization, scope, deconfliction, and safe-conduct standards for every operation, in partnership with the Associate Director and stakeholders.

• Operate and mature agentic AI red-team tooling: apply it to improve campaign planning, adversary research, and reporting quality; evaluate AI-assisted output for accuracy and operational fit; and feed practitioner requirements back to the Offensive AI Engineering team who build the platform.

• Test AI systems as targets: lead adversarial assessments of production AI-enabled systems, prompt injection (direct/indirect), agent/tool abuse, RAG/training-data poisoning, sensitive-data exposure, and guardrail/control bypass, including abusing an internal AI agent as a step toward a mission objective within a broader adversary-emulation campaign, mapped to the OWASP Top 10 for LLM Applications, MITRE ATLAS, and the NIST AI Risk Management Framework.

• Run purple-team engagements: measure detection and response (dwell time, alert fidelity, ATT&CK coverage) and drive detection-engineering improvements from what the campaign surfaced.

• Advise leadership on the direction of the red-team function; identify gaps in coverage and defensive controls; propose new adversary-emulation approaches for emerging threats.

Your first 6-12 months

• By 90 days: you've learned about our most complex prior campaigns and have had input on the planning/strategy for the next set, mapped the current state of our tradecraft and rules-of-engagement standards, and identified the first standards to raise.

• By 6 months: the team operates to methodology and RoE standards you've set; agentic AI tooling is integrated into at least one core red-team workflow, and you've led at least one adversarial assessment of a production AI system.

• By 12 months: AI-augmented red teaming and AI-system testing are a normal part of how the team works; you're advising leadership on the multi-quarter direction of the red-team function.

Use your skills to make an impact

Why this role, and why here

• Real authority over the craft. You set the tradecraft, own the rules of engagement, and engage with key enterprise and information security leaders, incorporating their input into campaign objectives and Red Team strategy.

• A program that's serious about AI . Red teaming here means both using AI to sharpen operations and testing the enterprise's own AI systems as adversarial targets, backed by a dedicated Offensive Platform/DevOps Engineering team building and integrating the tooling you help shape.

• A mission that matters. Every campaign tells the business whether it can actually detect and respond to a real adversary. Fridays for R&D, HTB Pro Labs, cert funding, conference budget.

What we're looking for

You do not need to check every box below. If you're a deep red-team operator and leader who's started testing AI systems and is ready to bring AI fluency to a team, we want to talk.

You'll need:

• 7+ years in red team, adversary emulation, or offensive security operations , with ~2 years leading complex operations or technical workstreams, setting the tradecraft and standards other operators follow.

• Deep adversary-emulation tradecraft. Objective-based operations across the full attack lifecycle (initial access, privilege escalation, lateral movement, defense evasion), hands-on C2 (e.g. Cobalt Strike, Brute Ratel, Nighthawk, and Mythic), and Active Directory / Entra ID attack paths, with a track record leading the most complex campaigns autonomously.

• Rules-of-engagement discipline. Y ou've owned the authorization, scoping, deconfliction, and safe-conduct standards that keep offensive operations legal and in-scope, and you can represent the red team's risk to security leadership.

• You've attacked AI. Hands-on adversarial testing of AI/LLM-powered systems (prompt injection, agent/tool abuse, jailbreaks), demonstrated ability to red-team emerging AI systems, or a strong red-team operator ready to build AI-attack capability and lead the team into it. We care about what you've done, not years on a framework that's only a few years old.

• You operate agentic AI tooling. You've used modern AI-assisted or agentic offensive tooling in real operations and can judge where it helps, or you're a strong operator ready to adopt it and lead a team's move toward it.

• You script. Advanced proficiency in Python, PowerShell, Bash, or Ruby for automation and custom red-team tooling.

• You translate operations into defensive impact. Purple-team debriefs, detection-engineering feedback, and executive-consumable risk narratives that change what the business does next.

Certifications are a plus, not a gate (e.g. OSCP, OSEP, OSED, OSCE3, CRTO, CRTL, or equivalent advanced credentials.)

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

• Contributing practitioner requirements to, or extending, agentic AI offensive tooling (multi-agent orchestration, MCP servers, LLM-as-judge) built by an AI-engineering team.

• Deeper adversarial ML, model extraction/inversion, membership inference, data/supply-chain poisoning, and hands-on with PyRIT or Garak.

• Malware development, custom tooling/implant development, or novel attack-chain research; published research or conference talks (DEF CON, Black Hat, BSides, x33fcon).

• Threat-intelligence-driven emulation (mapping APT/eCrime TTPs to campaigns) and detection-engineering collaboration.

How you'll work

You'll embed with our offensive service lines and set the rigor the red team operates to. You'll own, with the Associate Director and stakeholders, the authorization and rules of engagement for every operation, and the acceptable use of AI tooling in engagements. You lead the red-team craft; the Associate Director leads the people; the Offensive AI Engineering team builds the platform you help mature.

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.

$142,300 - $195,700 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: 08-09-2026

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.

Humana complies with all applicable federal civil rights laws and does not discriminate on the basis of race, color, national origin, age, disability, sex, sexual orientation, gender identity or religion. We also provide free language interpreter services. See our https://www.humana.com/legal/accessibility-resources?source=Humana_Website.