Senior Principal AI Testing Development

Coalfire is a cybersecurity company focused on solving complex security challenges, advising clients, and developing innovative security platforms. They are looking for a Senior Principal to lead AI integration in offensive security practices.

Location: Chicago, Illinois, USA

Salary: $226k–$250k

Responsibilities

• Deliver on complex application, network, and adversary services engagements.
• Architect and build AI-powered platforms and agentic systems for automating reconnaissance, attack discovery, exploitation, and reporting.
• Focus on outputs that improve profitability and efficiency.
• Lead secure software development, model integration, and platform engineering.
• Advise clients' senior leadership on security strategies.
• Collaborate with sales and marketing to grow the practice.

Requirements

• 10+ years of cybersecurity experience, including technical application and network pentesting, and red team engagements.
• Deep understanding of application penetration testing, assessment methodologies, and attack tradecraft.
• Knowledge of on-premise and cloud AD/identity misconfigurations and exploitation.
• Experience creating and delivering specialized testing and training on threat actor TTPs, APTs, ransomware, insider threats.
• Offensive services experience across various platforms and environments.
• Excellent communication skills for technical and non-technical audiences, including executives.
• Technical capabilities in complex penetration testing and adversary services.
• Experience developing scalable toolkits for engagements with ROI focus.
• Experience integrating ML pipelines and agents into offensive security work.
• Strong focus on ROI and impact on P&L.
• Ability to adapt in a fast-paced environment.
• Proficiency in Golang and Python, with ability to work across languages for ML pipeline integration.

Benefits

• Flexible work model.
• Support for personal and professional growth.
• Opportunities for community engagement and events.
• Competitive perks including paid parental leave, flexible time off, training reimbursement, mental health support, and insurance.