Penetration Tester

Wolf & Company, P.C. is looking for a Penetration Tester to support the DenSecure team with hands-on security testing and client-facing work from our Boston, MA onsite location. In this role, you will contribute to improving client security posture while also building your technical depth through ongoing testing engagements.

Why this role

• Hands-on testing focus: primarily manual, real-world penetration testing and security assessments.
• Client-facing impact: communicate testing approach, methodology, scope, and findings clearly to stakeholders.
• Rewards and growth: spot awards and a generous total rewards and benefits package, with eligibility for performance-based incentive compensation or sales commission plans.
• Supportive work environment: flexible work and strong emphasis on learning, teaching, and maintaining up-to-date testing knowledge.

Responsibilities

• Professional communication of the testing approach, methodology, scope, findings, and reporting details in both written and spoken formats.
• Write penetration test reports and related documents in a professional tone tailored to the appropriate audience.
• Conduct security assessments including internal network testing, external network testing, and social engineering. Social engineering may include phishing, vishing, and possibly physical testing.
• Maintain current knowledge of tactics, techniques, and procedures used during engagements and for ongoing client security posture improvement.

Requirements

• Absolute requirement: 1 to 2 years of working experience exclusively in penetration testing in a client-facing role, including testing in corporate production environments.
• Familiarity with standard attack paths and the ability to leverage open-source tools commonly used to target production environments (for example: Impacket, BloodHound, NetExec).
• Willingness to learn from others and teach others.
• Strong time management skills without reliance on micromanagement.
• Strong English communication skills (written and oral), including presenting report findings during meetings with C-Suite and upper management roles.

Tools and technologies

• Impacket
• BloodHound
• NetExec

Benefits

• Spot awards
• 401(k) savings
• Flexible work
• Generous total rewards and benefits package
• Performance-based incentive compensation or sales commission plans (eligible)

Nice to have qualifications

• OSCP/OSEP/OSAI/CRTO or other information security certifications demonstrating hands-on keyboard experience (proven technical skills are valued over certifications)
• Experience writing for or owning a technical blog
• Ongoing projects that enhance the team’s skill set
• A demonstrated specialty within the offensive security domain, such as maintaining basic testing infrastructure, web application skills, or social engineering proficiency

Location: Boston, MA (onsite). Compensation: USD 90,000 - 135,000 per year.