Senior Red Teamer (Cybersecurity)

TL;DR

Senior Red Teamer (Cybersecurity): Planning and executing full-scope offensive security engagements to simulate advanced persistent threats against the enterprise with an accent on custom tooling development and adversary simulation. Focus on conducting end-to-end red team lifecycles, mentoring junior staff, and collaborating with defensive teams to improve the organization's overall security posture.

Location: Must be authorized to work in the United States without sponsorship

Salary: $110,000–$160,000

Company

A diversified professional services and financial technology company with over 40 years of experience in student loan servicing, payments, and education solutions.

What you will do

• Own the full lifecycle of red team engagements, including scoping, threat modeling, execution, and post-engagement reporting.
• Conduct advanced penetration testing across web applications, APIs, cloud environments, and Windows Active Directory.
• Develop custom offensive tooling, exploits, and evasion techniques to support engagement objectives.
• Operationalize threat actor TTPs and translate findings into actionable attack chains and playbooks.
• Provide technical mentorship and guidance to junior red team practitioners through work reviews and knowledge transfer.
• Collaborate with blue team and SOC stakeholders to validate detection capabilities and deliver actionable feedback.

Requirements

• Must be authorized to work in the United States without current or future sponsorship.
• 5–8 years of hands-on experience in penetration testing or red team roles.
• Demonstrated experience leading red team engagements across network, cloud, and Active Directory domains.
• Proficiency in scripting and development (PowerShell, Python, C/C++, C#, or Bash).
• Experience operating and customizing command and control (C2) frameworks like Cobalt Strike or Sliver.
• Active industry certifications (OSCP, OSED, CRTO, CRTE, or equivalent).

Nice to have

• Experience with reverse engineering methodologies and tools (Ghidra, IDA, x64dbg).
• Familiarity with forensic methodologies for post-engagement analysis.
• Experience contributing to or publishing offensive security research.
• Prior experience in a formal mentorship or technical lead capacity.

Culture & Benefits

• Comprehensive benefits including medical, dental, and vision insurance.
• 401(k) plan with student loan repayment assistance.
• Generous earned time off and wellness programs.
• Tuition reimbursement and performance-based incentive pay.
• Supportive community-focused work environment.