People Operations Specialist

Must be based in Burlington, MA (Hybrid - 3 days/week in office)

Accelerate Your Career in Cybersecurity!

Pentera is the market leader in AI-native Security Validation, equipping enterprises with the platform to proactively test their defenses against the latest cyber attacks. Pentera proves which exposures are truly exploitable across the entire attack surface and drives remediation workflows that reduce real risk. Anchored in real-attack validation, the Pentera platform powers the full Continuous Threat Exposure Management (CTEM) cycle, from exposure discovery through prioritization, validation, and mobilization. Thousands of security teams around the world trust Pentera to close their security gaps before threat actors can exploit them. With over 350 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 a People Operations Specialist based in Burlington, MA, to own our US benefits infrastructure and deliver an exceptional employee lifecycle experience as Pentera scales worldwide. Reporting directly to the HR Business Partner, you will serve as the first point of contact for global employee queries across benefits, leave policies, onboarding, and HR processes. In this role, you will streamline operational workflows, build out our self-service HR portal, and partner across functions to keep our global workforce supported and engaged.

Responsibilities:

• Serve as the global first point of contact for routine employee People inquiries regarding benefits, leave policies, onboarding, employment documentation, and HR workflows.
• Lead US benefits administration end-to-end, managing enrollments, life-event changes, annual open enrollment, provider renewals, and day-to-day employee support.
• Own and execute operational employee onboarding and offboarding experiences to ensure seamless, high-quality transitions.
• Build and continuously improve the HR portal and self-service resources, including country benefit guides, FAQs, policy information, and onboarding materials.
• Partner closely with Payroll, Finance, Legal, IT, vendors, managers, and HRBPs to coordinate lifecycle workflows and resolve issues efficiently.
• Support broader People Operations activities, including performance-cycle administration, documentation management, and HRBP projects as needed.

• 3+ years of experience in People Operations or HR Operations within a growing technology environment.
• Hands-on experience with US benefits administration, open enrollment, leave management, and vendor coordination.
• Strong working knowledge of employee lifecycle processes, HR policies, and employment documentation.
• Proven experience building or maintaining employee self-service resources, HR portals, or knowledge bases.
• Demonstrated ability to collaborate cross-functionally with Payroll, Finance, Legal, and IT.
• Exceptional communication skills, strong attention to detail, and an empathetic, customer-centric approach to employee support.

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!