Director - Penetration Testing

| Austin
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Company Description 

Rapid7 (NASDAQ: RPD) is helping organizations around the globe advance securely. Our technology, services, and community-focused research simplify complexity for security teams, helping them reduce vulnerabilities, monitor for malicious behavior, investigate and shut down attacks, and automate routine tasks. With more than 9000 customers across 120+ countries, Rapid7 is a recognized leader in cybersecurity that has proudly earned numerous industry accolades and strong recognition for our technology and culture. Learn more at

Job Overview

Reporting to the Vice President of Security Services, the Director of the Penetration Testing business unit is a key member of the Security Services leadership team who possesses 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 coach, develop, and mentor subordinates to achieve quality performance while continuing to develop personal management skills necessary to lead staff and handle unique management challenges. The Director of Penetration Testing will advocate for their team as necessary in order for the team to successfully achieve its goals and objectives.

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

  • Promote employee development and continued growth, and participate in the development of strategies to find optimal solutions to compensate, attract, and retain the talent necessary to achieve established departmental and company goals and objectives.

  • Conduct formal and informal performance reviews and assist staff with establishing and attaining individual development goals.

  • 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+ years in a professional people management position

  • 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 is conveniently located in downtown Austin, with plenty of restaurants, bars, and public transport close by.

An Insider's view of Rapid7

What’s the vibe like in the office?

It has all the perks of a startup but well structured, goal driven, and supported growth as an employee from start to finish. Several places to relax or wind down after a call, and working in one of the most iconic buildings downtown. Welcome to the Austin office!


Customer Success Representative

What are Rapid7 Perks + Benefits

Volunteer in local community
Eat lunch together
Open office floor plan
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Retirement & Stock Options Benefits
401(K) Matching
Employee Stock Purchase Plan
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Fitness Subsidies
Professional Development Benefits
Job Training & Conferences
Promote from within
Time allotted for learning
Online course subscriptions available
Paid industry certifications
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