Director, Penetration Testing Services

Full Time
Boston, MA
Areas of Interest: Test and Evaluation
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Virtual / Telecommute
Remote work is frequently a way to describe working from a home office or being a telecommuter. Depending on the job and company, remote work offers the ability to work from anywhere in the world. To do a remote job, professionals need access to tools like phone/internet service and a quiet place to work without distraction.


Reporting to the Vice President of Global Services, the Director of the Penetration Testing business unit is a key member of the Global Services leadership team who possess a passion for customer success, technology and solving complex security problems with innovative solutions.  

This leadership role will help position, advise, and manage a line of business focused on defining state of the art security offerings that empower Rapid7 customers to understand and enhance their security programs and posture.  The Director of Penetration Testing will be responsible for developing a go-to-market strategy that leverages Rapid7’s differentiation to build meaningful, long-term customer relationships and develop high-impact, offensive service offerings.

The Director of Penetration Testing is expected to support the pre-sales process to attract and build our client base through sales enablement, service development, and scoping strategic opportunities. Their team will support customer relationships in both a pre- and post-sales capacity by delivering exceptional quality and mission-critical security solutions. The Director of Penetration Testing will work with customers and their teams to provide high-end/high-impact penetration testing services designed to provide customers with the insight required to improve their state of security. The Rapid7 Penetration Testing team should be seen by our customers as their long-term trusted source of advice for their security programs.

The Director of Penetration Testing will also collaborate with other Global Services leaders to foster collaboration, cohesion,and a consistent delivery approach not only across offerings (Incident Response and Strategic Advisory Services) but between APAC, EMEA and the Americas. This leader is expected to be highly visible in the security space and involved in driving thought leadership and innovation in the market. Responsibilities also include a focus on research, development, vulnerability disclosures, speaking events, conferences, and community involvement for their organization.

Compensation plan will include a variable component tied, but not limited to, Services performance metrics (bookings/revenue/margin), Services utilization and corporate performance.

Job Responsibilities

  • Establish clear market position, go-to-market approach and execution strategy for Rapid7’s Penetration Testing practice
  • Large scale P&L management and familiarity with Sales and Revenue forecasting
  • Directly support and drive opportunities and/or engagements from pre-sale through final delivery and sign-off 
  • Subject matter expert and advisor to Rapid7 Services’ Customers
  • Enable and energize pre-sales, sales, account management, and Channel Partners through clear value proposition and benefits, as a unique value roadmap, to meet the identified Customer business needs
  • Serve as subject matter expert with respect to market trends and competitor activities
  • Actively participate within Rapid7 community and security industry as advocate and advisor

Job Qualifications:

  • 10+ years professional services delivery or service provider in information security
  • 5-7 years experience delivering Penetration Testing Services at a large professional services firm
  • Bachelor's degree in a relevant discipline (Computer Information Systems, Information System Technologies, Management Information Systems) or related field
  • Consulting experience including interfacing and servicing clients, conducting proofs-of-concept, pre-sales technical scoping, managing and budgeting time and expenses, working in project-oriented environments with deadlines and milestones, making executive and technical presentations
  • Proven ability to build relationships with, understand business needs of, and deliver demonstrable value to senior management and C-level executives
  • Subject matter expert on regulatory guidance, best practices and key challenges organizations face from a security perspective
  • Willingness to travel up to 35% of the time

Job Plusses:

  • Published vulnerability disclosures, industry event presentations and/or tools, publications and methodologies
  • Preference to one of more professional certifications such as GPEN, GWAPT, OSCP, OSCE, CPT, CISSP, CISA, CISM
  • Locations: Boston, Austin, Washington D.C. preferable

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Rapid7 transforms data into insight, empowering IT and security professionals to progress and protect their organizations. How? Our solutions are powered by advanced analytics and an unmatched understanding of the attacker mindset. This makes it easy to collect data, transform it into prioritized and actionable insight, and get it to the people who can act on it—all in an instant. Our products and services enable organizations to innovate securely and reliably, and include offerings in vulnerability management (Nexpose), penetration testing (Metasploit), application security (AppSpider), SIEM/incident detection and response (InsightIDR), and log management (Logentries). Learn more at

Information Security, Vulnerability Management, Penetration Testing, Compromised User Detection, Mobile Risk Management, Enterprise Control Monitoring, Strategic Services, Security Programs, and Application Testing
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Company Industry: Computer & Network Security
Company Size: 501-1000