Technical Support Specialist (L2)

CharacterStrong; Auburn (WA); On-site; USD 55,000 - 75,000; Full time

Benefits offered by this job

New laptop and equipment

Professional development budget

401k with employer contributions

Medical, Dental, Vision Insurance

Life, AD&D, Disability Insurance

Employee Assistance Program

Parental leave

Flexible Time Off

Job summary

CharacterStrong is seeking a Technical Support Specialist (L2) to deliver advanced technical assistance to customers. You will resolve escalated issues, manage support inboxes, and handle inbound calls, collaborating with Product Management and Engineering to improve service quality.

The role requires strong troubleshooting, excellent communication, and solid IT systems knowledge, supporting both internal teams and external users in a fast-paced environment.

Qualifications

• 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.

Responsibilities

• 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 with Product Management, Engineering, and Infrastructure teams to elevate 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

Skills

Windows

macOS

Troubleshooting

Communication

Customer service

Tools

Microsoft 365

Teams

OneDrive

Outlook

Active Directory

Job description

Position Description: 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.

CharacterStrong's Background & Mission

CharacterStrong, a FullBloom Company, is a fast-paced, tech education company that makes PreK-12 digital, social-emotional learning curricula and offers professional learning opportunities to support schools with implementation. There’s currently a team of more than 130 full-time employees and over 40 contractors and interns collaborating to bring this work to life. Our mission is to create a more loving world by equipping educators with tools to teach the critical social, emotional, and character skills necessary to foster a more empathetic, connected, and generous world. In less than 10 years, our aim is to have reached 50 million students and over 2 million educators. We were ranked by INC. as the 449th fastest-growing private company in the country.

At CharacterStrong, you will have the opportunity to positively impact education, both in the United States and internationally. CharacterStrong employees offer their innovation, dedication to excellence, and compassion to help produce transformational curricula and professional learning for educators.

CharacterStrong’s Company Values & Norms

• We Produce Excellence - Producing timely, quality results and consistently asking the question, “How can we make this 1% better?”
• We Take Full Ownership - Taking the initiative to drive work forward, demonstrating responsibility when things do not go according to plan, and proactively closing identified gaps.
• We Practice Kindness - Exercising inclusion, care, and empathy with others, balancing honesty with compassion, and cultivating the well-being of self and others.
• We Problem-Solve - Identifying issues, analyzing for understanding, and taking action to implement the best possible solution.

Key Responsibilities

• 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 elevate 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

Other Duties

• Performs other duties as assigned.

Required Qualifications

• 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.

Benefit Package

• 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

CharacterStrong views diversity and the unique ways team members establish connections with our student and educator populations as an asset. Our goal is to ensure we have a team at CharacterStrong which reflects the diverse student population we serve.

CharacterStrong is an equal opportunity employer. We provide for fair treatment of all employees based on merit. In accordance with applicable law, race, color, creed, ancestry, national origin, citizenship, sex or gender (including pregnancy, childbirth, and pregnancy-related conditions, sexual orientation, gender identity or expression, and transgender status), marital status, religion, age, disability, genetic information (including testing and characteristics), service in the military, or any other characteristic protected by applicable federal, state, or local law does not affect employment opportunities or practices such as hiring, promotion, development opportunities, pay, or benefits. CharacterStrong complies with all applicable federal, state, and local labor laws. Learn more about us at CharacterStrong.com!