Penetration Testing Project Manager

Fortreum is a trusted leader in cloud and cybersecurity services, ranked among the Top 5 FedRAMP Third Party Assessment Organizations (3PAO). With the addition of Kovr.AI, we have expanded our capabilities to include advanced cyber risk quantification and analytics, enabling organizations to better understand, measure, and communicate risk. Together, we deliver independent, third-party, vendor-agnostic regulatory assessment and advisory services, alongside advanced cybersecurity offensive and compliance technical solutions. Our comprehensive service portfolio spans regulatory compliance frameworks including FedRAMP, CMMC, FISMA, SOC, PCI, ISO, and HIPAA.

Working with Fortune 500 companies and leading cloud service providers, we’ve built our reputation on service-delivery excellence and an unwavering commitment to client success. Our continued rapid growth creates exceptional opportunities for driven professionals to make their mark in the cybersecurity industry—guided by our core values: quality above all, a customer-driven mindset, autonomy, and personal accountability.

The Opportunity

Supporting Fortreum’s Override team, you will work alongside skilled offensive security professionals who test the defenses of cloud service providers, federal contractors, and technology companies. In this fast-paced role, you will manage multiple penetration testing engagements at once, moving quickly between clients, testers, and deadlines while delivering a high-touch, white glove experience. You will keep scoping, scheduling, client coordination, and reporting on track so our testers can focus on the work they do best.

Key Responsibilities

• Develop and maintain project plans for penetration testing engagements, including preparing pre-assessment documentation and templates such as Requests for Information (RFIs), kickoff presentations, Rules of Engagement (ROE), testing schedules, milestones, deliverables, and assigned responsibilities.

• Prepare and obtain signatures on rules of engagement, authorization letters, and other required planning documentation before testing begins.

• Schedule and lead client kickoff meetings, confirming scope, testing windows, points of contact, and communication and escalation procedures.

• Coordinate testing logistics with clients, such as test accounts, network access, allow listing, and notification of their security operations teams.

• Monitor and manage assessment scope to identify scope discrepancies and potential scope creep, coordinating with technical leads, clients, and the Program Manager to evaluate impacts, address changes, and ensure appropriate approvals are obtained.

• Manage communication of critical findings during testing according to agreed escalation procedures.

• Provide responsive, white glove service to clients as the primary point of contact, anticipating their needs and keeping them informed at every stage of the engagement.

• Execute high-velocity context switching by pivoting rapidly between engagements in different phases (scoping, active testing, reporting, retesting) without losing track of details or commitments.

• Reprioritize work as testing windows, client availability, and findings change, keeping stakeholders informed of any impact.

• Collaborate with other Project Managers to coordinate tester assignments across concurrent engagements, ensure balanced workloads, and work with the Program Manager to identify and resolve scheduling conflicts as needed.

• Track report development and quality review cycles to ensure reports are delivered on time.

• Monitor progress to ensure delivery within allocated hours, and assist team leads in validating budgets within financial management tools.

• Identify, track, and escalate risks, issues, and schedule concerns to leadership as needed.

• Maintain accurate project data in project management tools (for example, Jira).

• Complete engagement closeout, ensuring all deliverables and documentation are finalized and client data is handled according to policy.

• This is a client-facing role requiring strong communication and organizational skills. Limited travel may be required.

Basic Qualifications

• Bachelor’s degree or 4 years of equivalent experience

• 2 to 6+ years of experience managing multiple concurrent projects with internal teams and external clients, maintaining quality across parallel timelines.

• 2+ years of experience in information security, SaaS, or professional services.

• Experience supporting multiple penetration testing engagement types, such as network, web application, cloud, and social engineering testing.

• Understanding of penetration testing concepts and engagement types, such as network, web application, cloud, and social engineering testing, and the ability to discuss scope and findings with clients and testers.

• Ability to switch between tasks and engagements quickly while staying focused and accurate.

• Ability to manage competing priorities with flexibility and sound judgment.

• Excellent written and verbal communication skills, with a client-first approach to service.

• Skills in budget management, estimation, capacity planning, facilitation, and presentation.

• Proficiency with Microsoft 365 and project management tools (for example, Jira).

• Ability to work independently and thrive in a fast-paced team environment.

Preferred Skills

• Experience supporting FedRAMP penetration testing, readiness, authorization, or continuous monitoring efforts.

• Familiarity with security documentation such as SSPs, POA&Ms, and control implementation narratives.

• PMP, CAPM, or similar project management certification.