[Hiring] Pentest Manager @Thoropass

Role Description

We are looking for a Penetration Testing Manager to lead and mentor a sub-team of 4–5 pentesters within the Thoropass penetration testing organization. This is a player-coach position: you will perform hands-on pentests while ensuring your team stays motivated, on track, and consistently delivers high-quality results.

You’ll be part of a broader management structure with other Pentest Managers, working closely together to align methodologies, maintain consistency, and drive operational excellence across all teams. The ideal candidate combines strong technical expertise with people leadership skills, thrives in a collaborative environment, and enjoys developing others while still staying technically sharp.

Thoropass pentesters work with AI-augmented tooling as part of their daily workflow:

• AI handles the mechanical layer: reconnaissance enumeration, payload generation, finding drafts, and evidence formatting.
• The tester drives strategy, validates exploitability, and owns the final deliverable.

Qualifications

• 5–8+ years in pentesting or red teaming, including 1+ year of people management experience.
• Prior experience mentoring or managing security professionals.
• Strong technical expertise in web application, API, mobile, and network penetration testing.
• Working understanding of how to test AI-powered systems such as LLM applications, agents, and MCP-based integrations.
• At least 1 of the following certifications: OSCP, OSCE, OSWE, PWPT, Burp Suite Certified Practitioner.
• Knowledge of current attack methods, manual penetration testing techniques, and popular hacking tools.
• Proficient scripting skills in bash, Python, or similar languages.
• Fluency in English, with exceptional verbal & written communication.
• Strong sense of operational ownership.

Requirements

• Experience leading technical teams and understanding how to motivate, mentor, and empower others.
• Hands-on and comfortable switching between performing pentests and managing people.
• Thrives in fast-paced environments where structure and processes are actively evolving.
• Sets high standards for quality, leads by example, and brings a collaborative mindset to team leadership.

What You'll Do

• Lead and manage a Pentest team of 4–5 pentesters, providing technical guidance, feedback, and professional development support.
• Ensure all assigned engagements are delivered on time, within scope, and aligned with Thoropass standards.
• Conduct 1:1s, coaching sessions, and technical reviews to maintain motivation, quality, and team engagement.
• Collaborate with other Pentest Managers to balance workloads, share best practices, and standardize delivery processes.
• Partner with leadership to continuously improve internal operations, delivery frameworks, and team morale.
• Conduct web, network, API, LLM, and MCP penetration tests using various methods.
• Identify and exploit vulnerabilities to build realistic attack paths and show clear business impact.
• Produce detailed, customer-facing reports with practical remediation guidance.
• Stay current with modern attack techniques and tools.
• Help scale the pentest program through improved workflows, templates, and automation.
• Lead internal knowledge-sharing sessions and encourage a culture of continuous learning.
• Collaborate cross-functionally with Customer Success, Sales, and Operations.
• Support hiring, onboarding, and training as the pentest function expands.

Bonus Points

• Contributions to the security community, such as conference talks, blog posts, open-source projects, or CVE discoveries.
• Knowledge of compliance frameworks that often require pentesting (e.g., SOC 2, ISO 27001, PCI DSS, HIPAA).
• Experience working with cross-functional teams to scope, plan, or deliver pentests.
• Participation in bug bounty programs or vulnerability research initiatives.
• Experience with AI/LLM security testing and cloud environments such as AWS.
• Experience with Hack the Box, Portswigger Academy, or similar learning platforms.

Benefits

• Competitive base salary
• Exceptional private healthcare
• Early equity in a fast-growing company
• Work-from-home model
• Flexible PTO
• Home office equipment
• Monthly wellness and home Wi-Fi stipend

Equal Opportunity

Thoropass provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Even if you feel you don’t meet every requirement, consider applying! Thoropass acknowledges the research which shows that women and people of color are less likely to apply for jobs when they don’t meet all of the stated qualifications.