Manager, Penetration Testing (Massachusetts) at Rapid7

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Job 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


The Penetration Testing Team
Our team helps clients focus on security vulnerabilities and flaws that matter the most by applying a real world threat actor perspective to their attack surface. Within the team, we have expertise in nearly every discipline of offensive security from application testing, IOT, to red and purple team exercises. We partner with an organization's security, IT, audit, and business leaders to drive attack surface reduction through deep industry knowledge, offensive tradecraft, and expert consulting.

Our professionals must have the ability to handle complex situations and multiple responsibilities simultaneously in order to balance long-term projects while maintaining urgency on operational demands. They must also have an innate curiosity that drives offensive tradecraft development and execution in order to simulate real-world attack scenarios.


The Opportunity
Rapid7’s Penetration Testing team is looking for an experienced business and people leader with a firm understanding and experience in offensive penetration testing. This is an opportunity to join a leadership team and help shape the impact we have with our customers to drive continuous improvement on a global scale. Rapid7 is seeking a candidate that brings the right blend of leadership experience and execution skills to enhance our overall practice. If you are an energetic, innovative security leader, who has the experience and commitment to grow a global team, this could be a great match!
Essential Responsibilities
  • Develop and lead global programs focused on continuous improvement and evolution of pentest and offensive exercises
  • Drive business development through service innovation, client interaction, and sales support
  • Lead and develop a motivated team of managers and consultants
  • Engage directly with our customers to support an outstanding customer experience 
  • Collaborate with cross functional teams to drive integration, bundled services, and other opportunities for the team
  • Build upon Rapid7’s Services career framework to enhance the team’s focus on personnel development
  • Participate as a member of our global Security Services leadership team to collaborate as we evolve Rapid7’s customer experience
  • Evolve key processes across the teams to scale and drive customer value
  • Knows how to build sales leads and manage the scoping of deal pipeline
  • Knows how the business is run and can manage the intersection of sales support, sales pipeline, booking targets, and workload distribution.
Qualifications and Traits
  • 10+ years leading customer-facing penetration testing, red teaming, purple teaming, and offensive programs
  • Hands on experience conducting penetration testing and red teaming highly desirable
  • Prior experience designing security controls and defending networks/systems desirable
  • Experience working in global consulting organizations
  • 3+ years experience in a leadership position including managing managers
  • Dedicated cross-functional orientation and ability to build relationships with other leaders and teams
  • Creative problem-solving ability and forward-thinking mentality
  • Strong leadership and communication skills
  • Experience managing remote teams
  • Requires comprehensive understanding of concepts, theories and principles within offensive security testing and knowledge of other disciplines
  • Business leadership and relationship management experience with non-technical leaders and individual contributors
  • Creates formal networks with key decision makers and serves as external spokesperson for the organization
  • Understands how to work between tactical and strategic service design and delivery
  • Previous hands on technology design, architecture, and administration experience with network and systems infrastructure as well as middleware and applications
  • Professional certifications CISSP, CISA, GSEC, SSCP, CEH, ECIH highly desirable
  • Familiarity with security frameworks such as NIST, CIS, ISO, CMMC, etc. 
  • Outstanding verbal and written communication skills
  • Willingness to travel 25-40%

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Technology we use

  • Engineering
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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 some things you learned at the company?

It’s not just the customer who benefits from the culture of compassion. Internally, Rapid7 employees look out for each other and work together to solve problems. Oftentimes, this ends up helping all parties.


Senior Manager, Customer Success Management

What are Rapid7 Perks + Benefits

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Rapid7 is led by a diverse management team that represent the security community we serve. We believe that we all have a responsibility to continuously improve our DE&I efforts.
Unconscious bias training
We believe in continuous learning, our in-house trainers conduct consistent diversity trainings. We advocate for diverse thinking and strive to cultivate a workforce that mirrors the best minds.
Diversity Employee Resource Groups
We have so many amazing and organically created employee resource groups! These internal Rapid7 communities allow for an authentic experience where diverse employees and allies can come together.
Hiring Practices that Promote Diversity
We've taken the Parity Pledge, we reinforce strategic recruitment, we are committed to diversity partnerships, and we understand the importance in training around unconscious bias.
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Employee Stock Purchase Plan
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Our remote work program includes full-time remote for specific positions, Work remotely on occasion as needed.
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Our employees receive unlimited hours per year of paid volunteer time.
Paid Holidays
Paid Sick Days
Employees receive unlimited hours per year of paid sick leave.
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Game Room
Stocked Kitchen
Some Meals Provided
Employees get free lunch during quarterly in-office Town Halls and some team meetings.
Happy Hours
Fitness Subsidies
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Promote from within
Continuing Education stipend
Time allotted for learning
Online course subscriptions available
Paid industry certifications
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