Senior Cyber Tradecraft Engineer

Job Description

Job Description

Description:

Woven is hiring a Senior Cyber Tradecraft Engineer to lead access development, drive the team’s technical direction, and serve as the primary expert on digital tradecraft and access vectors for the program.

At this level, you’re not just executing test plans - you’re designing them. You’ll develop novel cyber methodologies, lead red team engagements against complex platforms, and translate findings into actionable solutions for federal customers. You’ll also mentor junior and mid-level specialists, set quality standards for documentation, and represent the team’s capabilities to customer leadership.

This role requires deep expertise in how online platforms work, combined with the offensive mindset to find where those systems break. You should have a proven track record of discovering vulnerabilities and communication skills to brief senior government stakeholders on findings and recommendations.

What you will do:

• Lead the development of novel technical approaches and cyber methodologies for assigned platforms, defining test strategies, success metrics, and evaluation frameworks
• Conduct advanced hands-on testing across platforms — designing multi-step access chains, identifying systemic vulnerabilities, and producing comprehensive findings for customer reporting
• Architect and maintain the team’s managed attribution infrastructure, establishing operational security standards and ensuring consistent tradecraft practices across all engagements
• Own and evolve the evaluation database — defining taxonomy, quality standards, and analysis frameworks that track technique effectiveness across customers and platforms over time
• Lead red team engagements against complex systems, coordinating multi-person operations and managing engagement scope with customer stakeholders
• Serve as the primary technical liaison to federal customer leadership on tradecraft capabilities, findings, and recommendations
• Collaborate with the internal ML team to evaluate AI models and tools, providing expert feedback on gaps, quality, and operational applicability
• Mentor junior and mid-level specialists — conducting technique reviews, leading training sessions, and developing the team’s overall skill level
• Stay ahead of the evolving cyber landscape, proactively identifying emerging technologies, evasion techniques, and regulatory shifts that impact the program
• Contribute to program strategy by identifying new capability areas, customer opportunities, and technical investments the team should pursue

Work environment:

• This role is based in Odenton, MD. A lot of the build work happens on low-side, but integration and deployment require hands-on access to classified systems that cannot be accessed remotely, so you will need to be on-site at customer facilities primarily.
• Travel is minimal. Expect 5–15% to Woven’s Virginia office and occasionally other locations for integration and deployment work. Some travel may be on short notice for operational needs.
• Schedule: Monday – Friday. Occasional after-hours work for time-sensitive operational testing, engagement execution, or technique validation.

Required qualifications:

• Active TS/SCI security clearance with CI Poly (must be current at time of application)
• U.S. citizenship (required for TS/SCI clearance)
• 7+ years of experience in cyber operations, penetration testing, red team operations, or digital tradecraft, with at least 3 years in a senior or lead capacity
• Proven track record of developing novel offensive methodologies — not just executing existing playbooks
• Extensive experience operating in digital environments under strict operational security controls, including managed attribution
• Strong leadership and mentorship skills — you elevate the team’s capabilities, not just your own
• Excellent documentation and communication skills: ability to produce detailed technical reports and brief senior government stakeholders on findings and recommendations
• Analytical rigor — you design systematic evaluation frameworks, not ad hoc testing

Preferred Qualifications:

• Experience leading red team engagements or adversarial security assessments 
• Deep knowledge of online platforms, account creation ecosystems, and how digital identity trust is established
• Experience with mobile platform security (iOS/Android), including app-level analysis and mobile authentication flows
• Background in fraud detection engineering or anti-fraud operations 
• Experience managing or contributing to classified research programs
• Relevant certifications: OSCP, OSCE, GXPN, GPEN, or equivalent advanced offensive security credentials