Director of Pentest Operations

We are Bugcrowd. Since 2012, we’ve been empowering organizations to take back control and stay ahead of threat actors by uniting the collective ingenuity and expertise of our customers and trusted alliance of elite hackers, with our patented data and AI-powered Security Knowledge Platform™. Our network of hackers brings diverse expertise to uncover hidden weaknesses, adapting swiftly to evolving threats, even against zero-day exploits. With unmatched scalability and adaptability, our data and AI-driven CrowdMatch™ technology in our platform finds the perfect talent for your unique fight. We aim to create a new era of modern crowdsourced security that outpaces threat actors. Unleash the ingenuity of the hacker community with Bugcrowd, visit www.bugcrowd.com. Based in San Francisco and New Hampshire, Bugcrowd is supported by General Catalyst, Rally Ventures, Costanoa Ventures, and others.

Job Summary

We’re hiring a Director of PTaaS Operations to lead delivery, automation, and innovation for our flagship offensive security service. This role owns the end-to-end lifecycle of PTaaS—from scoping and onboarding to execution and reporting—and is responsible for driving operational scalability, platform integration, and service excellence. You’ll lead a global team, deploy AI-powered automation, and be directly accountable for PTaaS growth targets. The ideal candidate will possess a growth mindset, a strong technical background, and a keen eye for process improvement and innovation. We’re looking for someone that can help scale operations through process improvement and automation.

This is your opportunity to industrialise one of the fastest-growing cybersecurity services on the market. You’ll work at the intersection of humans and machines, scaling offensive security for the enterprise with elegance and impact.

Duties & Responsibilities

Operational Excellence & Execution

• 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.

• Leadership & Management:
• 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..
• Continuous Improvement & 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.
• Client Engagement & Satisfaction:
• 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.

Education, Experience, Skills, & Abilities

• 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.
• Certifications such as CREST (e.g. CCT) OSCP, CISSP, or CISM preferred.
• Data-driven, customer-obsessed, and platform-savvy.

Working Conditions

The ideal candidate must be able to complete all physical requirements of the job with or without reasonable accommodation.

Sitting and/or standing - Must be able to remain in a stationary position 50% of the time

Carrying and /or lifting - Must be able to carry / move laptop as needed throughout the work day.

Environment - remote, work-from-home 100% of the time.

ADA Statement

Bugcrowd is committed to the full inclusion of all qualified individuals. In keeping with our commitment, Bugcrowd will take the steps to assure that people with disabilities are provided reasonable accommodations. Accordingly, if reasonable accommodation is required to fully participate in the job application or interview process, to perform the essential functions of the position, and/or to receive all other benefits and privileges of employment, please contact HR at ada@bugcrowd.com.

Culture

• At Bugcrowd, we understand that diversity in the workplace is vital to a company’s success and growth. We strive to make sure that people are included and have a sense of being part of making Bugcrowd not only a great product but a great place to work.
• We regularly hear from both customers and researchers that Bugcrowd feels like a family, and we strive to maintain that internally as well.
• Our team consists of a broad range of people: musicians, adventure sports junkies, nature lovers, parents, cereal enthusiasts, night owls, cyclists, artists—you get the point.

At Bugcrowd, we are solving security threats and vulnerabilities that are relevant to everyone, therefore we believe solving these problems takes all kinds of backgrounds. We value the perspectives and experiences people from underrepresented backgrounds bring.

Disclaimer

This position has access to highly confidential, sensitive information relating to the technologies of Bugcrowd. It is essential that the applicant possess the requisite integrity to maintain the information in the strictest confidence.

The company is authorized to obtain background checks for employment purposes under state and federal law. Background checks will be conducted for positions that involve access to confidential or proprietary information (including trade secrets).

Background checks may include Social Security verification, prior employment verification, personal and professional references, educational verification, and criminal history. Applicants with conviction histories will not be excluded from consideration to the extent required by law.

Equal Employment Opportunity:

Bugcrowd is EOE, Disability/Age Employer. 

Individuals seeking employment at Bugcrowd are considered without regards to race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. 

Apply at: https://www.bugcrowd.com/about/careers/