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The Technical Support Specialist (L2) provides advanced technical support to CharacterStrong customers, ensuring the timely resolution of escalated issues that cannot be resolved by Level 1 support. This role requires strong troubleshooting skills, excellent communication, and a solid understanding of contemporary IT systems. The specialist will work closely with internal Technology teams—including Product Management and Engineering—to maintain service quality, minimize downtime, and deliver a consistently positive support experience. The position is customer-facing and includes managing customer support inboxes and handling inbound support calls.
Job Responsibility:
Troubleshoot and resolve advanced technical issues related to operating systems (Windows, macOS, Linux), user accounts, security permissions, and device configurations
Support enterprise applications such as Microsoft 365, collaboration tools, and line-of-business systems
Administer and troubleshoot Active Directory, Group Policy, and identity/access management tools
Assist with network connectivity issues, including VPN, Wi-Fi, and basic switch/router configurations
Document troubleshooting steps, resolutions, and knowledge-base articles for recurring issues
Monitor and manage assigned customer support inboxes, ensuring messages are triaged, prioritized, and resolved efficiently
Collaborate closely with Product Management, Engineering, and Infrastructure teams to escalate product defects, clarify expected functionality, and share customer insights
Mentor and support Level 1 Support Specialists by providing guidance, coaching, and technical knowledge-sharing
Participate in on-call rotations or after-hours support as required
Uphold a customer-first mindset while balancing efficiency, accuracy, and technical depth
Requirements:
3-4 years of experience in a technical support or helpdesk environment
Strong knowledge of Windows and macOS operating systems
Proficiency with Microsoft 365, Teams, OneDrive, Outlook, and related applications
Experience with Active Directory, user provisioning, and basic networking concepts
Solid understanding of IT security best practices and endpoint protection tools
Excellent analytical and problem-solving skills
Strong verbal and written communication abilities
Ability to work independently and handle multiple tasks in a fast-paced environment
What we offer:
New laptop computer and other needed equipment
Annual Individual Budget for Professional Development of $1,000
401k Savings Plan with employer contribution
Medical, Dental, & Vision Insurance
Life, AD&D, and Disability Insurance
Employee Assistance Program, Mental Health Support, and Well-Being Programs
3 weeks Company-Paid Parental Leave (after 6 months of active employment)
Flexible Time Off, 6 Paid Sick Days, 11 Paid Company Holidays