Director of Pentest Operations

Summary

Join Bugcrowd as the Director of PTaaS Operations to lead the delivery, automation, and innovation of our flagship offensive security service. You will oversee the entire PTaaS lifecycle, from initial scoping and onboarding to final execution and reporting, driving operational scalability, platform integration, and service excellence. Lead a global team, implement AI-powered automation, and be directly responsible for achieving PTaaS growth targets. The ideal candidate will have a growth mindset, a strong technical background, and a keen eye for process improvement and innovation. This role offers the opportunity to industrialize one of the fastest-growing cybersecurity services, working at the intersection of humans and machines to scale offensive security for enterprises. You will partner with various teams to support PTaaS adoption, expansion, and retention, while ensuring accurate data and metrics reporting to drive growth and optimization.

Requirements

• 10+ years in cybersecurity services or SaaS operations, with direct experience in pen testing or PTaaS preferred
• 3+ years in a senior operational or service delivery leadership role
• In depth technical understanding of pentesting approaches across multiple target types
• Demonstrated success leading complex, fast-moving operational functions with automation at scale
• Strong grasp of pen test lifecycle, customer needs, and platform-enabled delivery models
• Experience deploying or managing AI/ML capabilities within operational workflows
• Data-driven, customer-obsessed, and platform-savvy

Responsibilities

• Own operational delivery for all PTaaS engagements—project launch, execution, QA, and reporting
• Partner with Sales, Product, and Marketing to support PTaaS adoption, expansion, and retention
• Deliver against defined KPIs (cycle time, margin, CSAT) and support ASG revenue contribution targets
• Design, refine, and scale PTaaS delivery workflows tightly coupled to Bugcrowd’s platform
• Integrate automation for engagement setup, researcher matching, submission and quality triage, and client communications
• Collaborate with Product to influence tooling that accelerates service throughput and consistency
• Ensure accurate data and metrics reporting to allow insights into the business that drive growth and optimisation
• Partner with VP, Advanced Services and other Directors to drive the strategic direction and operational excellence of the Advanced Services division
• Lead a high-performing, globally distributed PTaaS operations team—including engagement managers and pen testers
• Foster a collaborative and inclusive team culture of precision and accountability that promotes continuous improvement and innovation
• Deploy AI/ML capabilities to enhance workflow automation, reduce analyst toil, and boost engagement velocity
• Lead pilot programmes to test and adopt new delivery models, tools, and quality assurance mechanisms
• Stay ahead of the curve on AI-driven security ops, continuous testing trends, and emerging delivery techniques
• Champion a culture of continuous improvement and proactive problem-solving
• Identify and implement new methodologies, tools, and technologies to enhance service offerings
• Stay abreast of industry trends, emerging threats, and best practices in cybersecurity
• Maintain strong relationships with key clients, ensuring their security needs are met and expectations exceeded
• Address and resolve any client issues or concerns promptly and effectively
• Provide expert guidance and support to clients on security best practices and risk mitigation strategies

Preferred Qualifications

Certifications such as CREST (e.g. CCT) OSCP, CISSP, or CISM preferred

Benefits

Remote, work-from-home 100% of the time