Lead, Offensive Security

CenterWell Primary Care$142K — $195K *
US-AnywhereRemote in United States
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 7+ years in red team or offensive security operations, with ~2 years in leadership roles
  • Expertise in adversary-emulation methods across the attack lifecycle
  • Experience establishing rules of engagement for offensive operations
  • Hands-on background in adversarial testing of AI systems
  • Advanced scripting skills in Python, PowerShell, or similar languages
  • Ability to translate tactical operations into strategic defensive recommendations

Responsibilities

  • Set and govern the team's adversary-emulation methodology and standards
  • Lead complex red-team campaigns with full autonomy
  • Define and manage rules of engagement for all operations
  • Utilize agentic AI tooling to enhance red teaming strategies
  • Conduct adversarial assessments of AI-powered systems
  • Facilitate purple-team engagements to improve detection and response
  • Advise leadership on strategic direction for the red-team function

Benefits

  • Comprehensive medical, dental, and vision coverage
  • 401(k) retirement savings plan
  • Generous paid time off including holidays and parental leave
  • Short-term and long-term disability insurance
  • Life insurance and wellness programs
  • Certification funding and a dedicated conference/training budget for professional development
Full Job Description
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 teamoperates and maturesagentic 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 6 612 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

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. You'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 employees92 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, 9cHumana9d) 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 CenterWell Primary Care

CenterWell Primary Care Careers

Joining CenterWell Primary Care presents an unparalleled opportunity to advance one's career in a leading healthcare organization that is dedicated to innovation and quality care. CenterWell Primary Care is actively seeking professionals who are passionate about making a difference in the healthcare industry.

Explore Job Opportunities

CenterWell Primary Care offers a variety of job opportunities that enable professionals to grow their careers in an environment that values leadership and diversity. The company is committed to fostering a culture where innovation thrives and leadership skills are honed.

Professional Growth and Development

At CenterWell Primary Care, career growth is a priority. The company supports professional development through comprehensive training programs and opportunities for advancement. Employees are encouraged to expand their skills and knowledge, positioning themselves as leaders in the healthcare sector.

Diversity and Inclusion

CenterWell Primary Care is dedicated to creating a diverse and inclusive workplace. The company believes that diversity training and an inclusive culture are key to innovation and the delivery of exceptional care. Employees from various backgrounds bring unique perspectives that enhance the team's performance and patient outcomes.

Benefits and Culture

Employees at CenterWell Primary Care enjoy a range of benefits designed to support their professional and personal lives. The company's culture is centered on teamwork, respect, and integrity, providing a solid foundation for personal growth and job satisfaction.

Internship Programs

For those starting their career, CenterWell Primary Care offers internship programs that provide hands-on experience in the healthcare field. Interns gain valuable insights and skills, which are crucial for building a successful career in healthcare.

Hiring Process

The hiring process at CenterWell Primary Care is designed to identify candidates who are not only skilled but also passionate about making a difference in healthcare. Prospective employees can expect a thorough interview process where they can showcase their skills and learn more about the company's mission and values.

Networking and Professional Opportunities

CenterWell Primary Care encourages its team to engage in networking opportunities within and beyond the company. This engagement fosters professional connections and collaborative opportunities that can lead to innovative solutions and enhanced patient care.

Join the Team

CenterWell Primary Care is looking for curious, creative, and solution-driven team players. Search open positions that match your skills and interests on the CenterWell Primary Care Jobs page. Tailor your resume to reflect your expertise and prepare for a career that promises both professional and personal growth.

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Discover the rewarding opportunities awaiting at CenterWell Primary Care. With a commitment to employee growth, a diverse culture, and a drive for innovation, CenterWell Primary Care is the perfect place to advance your career in healthcare.
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