Customer Success Team Leader

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’ll be at the forefront of cybersecurity innovation, working on advanced tools that challenge organizations' defenses and push the limits of security testing.

With over 350 team members and 1,000+ customers in more than 50 countries, Pentera is a growing company supported by top investors like Insight Partners, K1, and The Blackstone Group.

If you're looking to grow your skills, make a difference, and be part of an innovative team, Pentera is the place for you.

About the role:

Pentera seeks a Customer Success Team Leader who excels in cultivating outstanding customer relationships and possesses a unique combination of passion, experience, people-centered leadership, and a proven history of steering organizational change.

As a player/coach, the Customer Success team leader will lead and mentor a team of approximately four Customer Success Managers, while also managing their own portfolio of strategic accounts. You will ensure customer satisfaction, retention, and revenue growth through effective relationship management, renewals, and expansion opportunities.

Pentera partners with some of the largest and most recognizable enterprises worldwide, so experience managing global enterprise accounts is essential.

Roles and Responsibilities:

• Lead, coach, and inspire a team of Customer Success Managers through mentorship and performance management.
• Cultivate and maintain strong relationships with senior stakeholders, acting as a trusted advisor and ensuring customers realize measurable value.
• Drive contract renewal negotiations and identify upsell/cross-sell opportunities.
• Develop and implement strategies to improve retention, reduce churn, and maximize customer lifetime value.
• Monitor engagement and health metrics, delivering tailored success plans and mitigating risks.
• Define, track, and report on KPIs such as adoption, satisfaction, retention, and revenue contribution.
• Partner closely with Sales, Product, Support, and Customer Operations to advocate for the customer voice and ensure alignment.
• Travel as required to customer sites to strengthen relationships and drive strategic alignment.

• 5–8 years of experience in Customer Success, Account Management, or related roles, with a strong track record of managing high-value customer relationships and renewals.
• Proven leadership experience, including team management, coaching, and development.
• Experience managing global enterprise accounts
• Background in cybersecurity or SaaS/tech environments.
• Demonstrated success in negotiating complex contracts and driving revenue growth.
• Exceptional communication, presentation, and negotiation skills, with executive presence.
• Strong analytical and problem-solving abilities; comfortable navigating complex customer challenges.
• Willingness and ability to travel frequently for customer engagements, in the region
• Bachelor’s degree in a relevant field required; advanced degree or MBA is a plus.

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!