Manager, Offensive Security

About the role

Gainsight is seeking a full‑time Manager, Offensive Security to lead red and purple team assessments and other offensive cyber engagements. Reporting to the Chief Security Officer, you will work remotely across the United States, collaborating with engineering, IT, legal, and product teams to protect both Gainsight and its customers.

Key responsibilities

• Design and execute red‑team, purple‑team, and assumed‑breach assessments, including ransomware readiness reviews.
• Conduct external and internal wireless, web, mobile, cloud, and embedded system security testing.
• Research and develop offensive tools, incorporate threat‑actor intelligence, and share findings internally.
• Produce detailed technical reports and executive‑level presentations.
• Occasionally travel (up to 10%) for team meetings, training, or company events.

Required profile

• 5‑7 years of relevant experience, including recent management experience.
• At least 5 years of hands‑on penetration testing and red‑team work covering network, web, mobile, cloud, and social engineering.
• Proven ability to work cross‑functionally in a fast‑growing environment.

Required skills

• Red teaming and purple teaming
• Penetration testing (network, web application, mobile, cloud)
• Wireless security assessment
• Embedded system security testing
• Social engineering techniques
• Scripting and offensive tool development
• Threat analysis and ransomware readiness assessment

What we offer

• Opportunity to shape the offensive security practice of a leading AI‑driven customer success platform.
• Collaboration with a high‑performing, cross‑functional security team.
• Remote work flexibility.