Penetration Tester (Contract)

Educate 360; Northern (KY); On-site; USD 90,000 - 140,000; Part time

Job summary

Educate 360 is seeking several contract penetration testers to grow our offensive security practice. The role spans mid to senior levels, with autonomy to perform assessments and deliver reports.

Strong client interaction and SME debriefs are valued, with potential conversion to full-time. The position requires at least 3 years of hands-on testing across external, internal, cloud, and red team engagements, plus relevant certifications such as PNPT, OSCP, CREST CRT, or CPTS.

Qualifications

• At least 3 years of penetration testing experience.
• Experience with external/internal testing, cloud assessments, and red team engagements.
• Industry-standard certifications such as PNPT, OSCP, CREST CRT or CPTS.

Responsibilities

• Conduct assessments and write reports with minimal oversight.
• Debriefs and manage client interactions as SME in offensive security.

Skills

Penetration testing

External testing

Internal testing

Cloud security assessments

Red team engagements

PNPT

OSCP

CREST CRT

CPTS

Client-facing

Report writing

Job description

All Jobs > Penetration Tester (Contract)

Brand: TCM Security

About Educate 360

Educate 360 is a family of specialized training brands with a joint mission: to help individuals and organizations gain the skills needed to thrive in today’s technology-led and innovation-driven economy. Educate 360 develops integrated solutions across brands to achieve enterprise customers’ learning & development goals in Management & Leadership, Data Science, and IT skills —through instructor-led training, coaching, consulting, and certification preparation.

Role Summary

TCM Security is hiring several contractors to help grow our penetration testing practice. Candidate experience may range from mid-level penetration testers to senior or principal-level candidates. The ideal candidate should be a self-starter with a passion for offensive security and experience across multiple project types. This role has the potential for conversion to a full-time position

Requirements

Have at least 3 years of penetration testing experience, including but not limited to:

• External penetration testing (preferred)
• Internal penetration testing (preferred)
• Cloud security assessments
• Red team engagements
• Hold industry standard penetration testing certifications such as PNPT, OSCP, CREST CRT, CPTS or other related certifications.
• Enjoy working with new clients weekly and interacting with clients daily, serving as a Subject Matter Expert (SME) in offensive security remediations and attack vectors. Strong preference is given to candidates with extensive experience conducting debriefs and managing client interactions.
• Love learning and sharing new attack vectors and knowledge about the fields of offensive security and information security.
• Work well with a high degree of autonomy to conduct assessments and write reports with minimal oversight.
• Must be US-based

Why Educate 360?

We believe that great ideas emerge when people collaborate in an environment where thoughts and perspectives can be freely shared. Effective teamwork happens when every member feels empowered, valued, and respected. We are committed to fostering a culture where everyone is accepted, included, and encouraged to contribute in meaningful ways.

Equal Opportunity Employer:

Educate 360 is committed to providing equal employment opportunity for all persons regardless of race, color, religion, sex, age, marital status, national origin, citizenship status, disability, or veteran status.