Accelerate Your Career in Cybersecurity! Join Pentera and take your career to the next level in cybersecurity. As a leader in Automated Security Validation, we help businesses around the world safely emulate real-world attacks to uncover their vulnerabilities, just like the world’s best red teams. At Pentera, you will be at the forefront of cybersecurity innovation, working on advanced tools that challenge organizations' defenses and push the limits of security testing. With over 400 team members and 1,300 customers in more than 60 countries, Pentera is a growing company supported by top investors such as Insight Partners, K1, and The Blackstone Group. If you want to grow your skills, make an impact, and be part of an innovative team, Pentera is the place for you. About the role: We're looking for an experienced, customer-obsessed Senior Director, Technical Support to lead Pentera's global Technical Support domain and scale the people, processes, and AI-driven technology behind it as we grow. Reporting to the Chief Customer Officer, you'll lead a global team of ~20 support engineers and partner closely with Customer Success, R&D, Product, and Sales Engineering to ensure every enterprise customer gets exceptional technical guidance. A core part of the mandate is modernizing how we support customers — leveraging AI, automation, and self-service to scale quality without scaling headcount linearly. You'll bring deep technical understanding of enterprise software and cybersecurity, strong operational leadership, and a track record of building high-performing global teams. Responsibilities: Lead and develop Pentera's global Technical Support organization: hire, coach, and grow TLs and individual contributors, and build a culture of ownership, technical excellence, and continuous learning. Own global support operations and strategy end to end, delivering fast, consistent, high-quality outcomes across regions and time zones, backed by scalable processes and or