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Senior Penetration Tester

Wolf & Company, P.C.

Wolf & Company, P.C.

Boston, MA, USA
USD 120k-180k / year
Posted on Jan 13, 2026

Senior Penetration Tester

Location US-MA-Boston
ID 2026-1489
Category
DenSecure (DNS)
Position Type
Full-Time

Overview

Wolf is seeking a Senior Penetration Tester to join our growing and well-established national firm. As a Penetration Tester, you will help support the DenSecure team through a variety of tasks related to delivering and enhancing various security services provided to our clients. The successful candidate possesses strong communication skills, has a desire to be challenged in a dynamic work environment, and is looking to find a place to continue their career within a rapidly growing team.

*This is a remote role. Candidate must be willing to work EST hours if needed.

Responsibilities

  • Perform a variety of security assessments, including internal, external, assumed breach, and social engineering to include phishing, vishing, etc.
  • Provide recommendations for enhancements to clients’ security environments to prevent successful attacks, whether related to specific deficiencies identified in testing or general best practice
  • Be a technical go-to for testers with less experience

Qualifications

Necessary Qualifications:

  • Must have at least two (2) years of working experience in penetration testing (this is an absolute must to be considered). This experience must involve testing corporate environments that leverage Active Directory, Microsoft 365, etc.
  • Be willing to learn from and teach others
  • Strong curiosity and desire to bolster the team’s agreed-upon future objectives
  • Mature time management skills without the need for “micromanagement”
  • Strong English communication skills (written and oral) – you will be required to present report findings during meetings with C-Suite and upper management roles

Nice to Have Qualifications:

  • Prior experience in consulting, client facing role working with various stakeholders
  • OSCP or other information security certifications that prove “hands on keyboard” knowledge
  • Write for or own a technical blog
  • Compete in CTF competitions, Hack the Box, or other platforms
  • Have ongoing projects that can enhance the team’s skill set
  • Maintaining “red” team infrastructure used for C2 and social engineering

Additional Information

Wolf & Company, P.C. is committed to striving to be an employer of choice that embraces inclusion & diversity. At Wolf, the strength of our team is measured by the uniqueness of each and every one of us. Our culture of inclusion and diversity celebrates our differences and recognizes the ongoing need to build a welcoming, collaborative, and supportive environment where our people can be their authentic selves and thrive. We strive for diversity inclusive of race, color, ethnicity, national origin, gender identity, gender expression, sex, age, color, religion, sexual orientation, physical abilities, medical condition, pregnancy, education, social classes, marital status, veteran status, and so much more. Wolf is committed to making employment decisions without regard to an individual’s protected characteristics and to providing equal opportunity for all.

The salary range for this position is 120,000 - $180,000.

Actual compensation within the range will be dependent upon the individual's skills, experience, qualifications and location, and applicable employment laws. In addition to base pay, you may be eligible to participate in our performance-based incentive compensation or sales commission plans. In addition, Wolf offers a wide range of benefits including spot awards, 401(k) savings, flexible work, and a generous total rewards and benefits package.

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