Technical Support Specialist; L2

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The Technical Support Specialist (L2) provides advanced technical support to Character Strong customers, ensuring 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 works 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.

Character Strong, a Full Bloom Company, is a fast‑paced tech‑education company that creates PreK‑12 digital, social‑emotional learning curricula and offers professional learning opportunities to support schools with implementation. With a team of more than 130 full‑time employees and over 40 contractors and interns, Character Strong’s 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, the company aims to have reached 50 million students and over 2 million educators and was ranked by INC. as the 449th fastest‑growing private company in the country.

• We Produce Excellence – producing timely, quality results and consistently asking "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.

• 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.

• Performs other duties as assigned.

• 3–4 years of experience in a technical support or help‑desk environment.
• Strong knowledge of Windows and macOS operating systems.
• Proficiency with Microsoft 365, Teams, One Drive, 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.

• New laptop computer and other needed equipment
• Annual individual budget for professional development of $1,000
• 401(k) savings plan with employer contribution
• Medical, dental, & vision insurance
• Life, AD&D, and disability insurance
• Employee assistance program, mental health support,…