Senior Director Technical Support

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.

Roles and 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 organizational design that keep pace with our growth.
• Lead the AI transformation of the support function: deploy AI-driven workflows, automation, and self-service to speed up resolution, deflect volume, and scale quality without scaling headcount linearly.
• Own the support KPIs: SLA compliance, CSAT, response and resolution times, backlog health, and escalation management.
• Be the bridge between customers, Support, Product, and R&D: surface critical escalations, make the case for the fixes that matter, and influence the product roadmap.
• Serve as the executive escalation point for complex customer issues, coordinating cross-functional resolution when required.
• Partner with Customer Success, Professional Services, Sales Engineering, and Sales to deliver a seamless end-to-end customer experience.

• 10+ years leading global enterprise Technical Support organizations in B2B SaaS or cybersecurity, including managing managers across regions and time zones.
• Track record of scaling support organizations in high-growth environments.
• Technical background supporting complex enterprise software, infrastructure, cloud, networking, or cybersecurity solutions.
• Experience leading AI-driven support: automation, self-service, and modern tooling that scale quality as the organization grows.
• Experience building operational excellence through metrics, dashboards, and process improvement.
• Strong cross-functional influence: pushing customer and support needs into Product and R&D and driving resolution across teams.
• Outstanding leadership, coaching, and stakeholder management, including work with executives and strategic customers.
• Ability to balance strategic thinking with hands-on execution. Fluent English.
• Advantage: experience with CRM and support platforms such as Salesforce, Zendesk, or Jira.

We are an equal opportunity employer and we are committed to building a diverse and talented workforce. We do not discriminate on the basis of race, sex, religion, colour, national origin, gender, gender identity, sexual orientation, age, marital status, veteran status, medical condition, disability, or any other class or characteristic protected by applicable law. We welcome candidates from all backgrounds to join us!