Manager, Offensive Security

We’re building the AI-driven future of customer success, from retention to growth! We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link . About This Role: We’re looking for a full-time Manager, Offensive Security to join our security team reporting to the Chief Security Officer. This role is a remote role based in the United States. In this role, you’ll play a key role in by performing Red and Purple Team assessments, including adversarial emulation of cyber attacks against customer organizations, and other technical cyber assessments including external pen testing, web application, mobile, and wireless security testing. You will expand the team’s capabilities through tool creation, research on offensive techniques, incorporation of threat actor intelligence, internal presentations, and knowledge sharing. This is a great opportunity for someone who thrives in a high performing growth environment and enjoys working cross-functionally with teams like engineering, IT, legal and product. What You'll Do: Perform red and purple team assessments, assumed breach assessments (e.g., red team engagements with a pre-deployed implant), ransomware readiness reviews (e.g., assessing susceptibility to modern ransomware threats), threat analysis, and social engineering assessments. Conduct external and internal wireless assessments, web and mobile applications testing, and embedded system assessments. Recognize and safely utilize attacker tools, tactics, and procedures. Develop comprehensive and accurate reports and presentations for both technical and executive audiences. Perform offensive technical cyber security engagements of a varied nature. This role may require occasional travel (up to 10%) for team meetings, training, or company events. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. What We're Looking For: 5-7 years of relevant experience (or equivalent combination of education and experience), including recent management experience required. 5 years of experience with pen testing and red teaming functions, including network, web application, mobile, cloud, social engineering, scripting, or tool development. Experience with tools used for wireless, web application, and network security testing. Nice-to-have Skills: Certifications related to offensive security including OSCE, OSEP, OSEE, OSCP, CCSAS, CCT, INF, or relevant SANS courses. Experience implementing or assessing information security implementation or assessment of security controls. Why You’ll Love It Here: Gainsight is a place where innovation is shaped through collaboration, curiosity, and a shared focus on solving real-world problems. With a growing suite of products across customer success, product experience, community, education, and AI-powered relationship intelligence, we continue to evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few: Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported. The starting base salary range for this role is $160,000 - $200,000 USD annually. This role is also eligible for commission based on performance and participation in Gainsight’s equity program. Actual compensation may vary based on factors such as skills, experience, and location. We offer a comprehensive benefits package including fully covered medical premiums (employee-only), flexible PTO, 401(k) plan, dental and vision coverage, and remote work options. Additional benefits include a $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset. Our Core Values : We are guided by our values and our mission to be living proof you can win in business while being Human-First . Learn more here . Our Growth Opportunities : From mentoring to career development opportunities, we’re passionate about helping our teammates learn, grow, and thrive. Our Parody Videos : No explanation needed. Just watch them here! If this sounds like the right role for you, we’d love to hear from you. Additional Information: We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates. If you require accommodations or have questions about how your personal data will be used during the hiring process, please contact [email protected] . If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.