L2 Tech Support Engineer — Windows/macOS & 365

CharacterStrong, LLC; Auburn, Northern (WA, KY); Hybrid; USD 65,000 - 90,000; Full time

Benefits offered by this job

New laptop

Professional development budget

401k employer contrib

Medical, Dental, & Vision Insurance

Life/AD&D/Disability

Well-being programs

Parental leave

Flexible PTO & holidays

Job summary

CharacterStrong, LLC in Washington state seeks a Technical Support Specialist (L2) to deliver advanced, customer-facing IT support. You will diagnose complex issues, support Microsoft 365 apps, AD, and security tools, and mentor Level 1 peers.

Collaborate with Product Management and Engineering to improve services while maintaining high customer satisfaction. This role requires strong troubleshooting, clear communication, and the ability to manage multiple incidents with urgency and accuracy in

Qualifications

• 3-4 years of experience in technical support or helpdesk.
• Strong knowledge of Windows, macOS, and Linux OS.
• Proficiency with Microsoft 365, Teams, OneDrive, Outlook.
• Experience with Active Directory, user provisioning, and basic networking concepts.

Responsibilities

• Troubleshoot and resolve advanced technical issues related to operating systems, 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 and resolved.
• Collaborate with Product Management, Engineering, and Infrastructure teams to elevate product defects and share customer insights.
• Mentor and support Level 1 Support Specialists; participate in on-call rotations.

Skills

Troubleshooting

Communication

Time management

Team collaboration

Independent work

Tools

Microsoft 365

Teams

OneDrive

Outlook

Active Directory

Networking basics

Endpoint protection

Job description

CharacterStrong, LLC in Washington state seeks a Technical Support Specialist (L2) to deliver advanced, customer-facing IT support. You will diagnose complex issues, support Microsoft 365 apps, AD, and security tools, and mentor Level 1 peers.

Collaborate with Product Management and Engineering to improve services while maintaining high customer satisfaction. This role requires strong troubleshooting, clear communication, and the ability to manage multiple incidents with urgency and accuracy in