Tech Support Specialist II

Company Overview

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.

Overview

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.

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 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
    

Other Duties

• • Performs other duties as assigned.

 

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.

Posted Salary Range

USD $70,000.00 - USD $85,000.00 /Yr.

Requires 3–4 years in technical support or helpdesk, Windows and macOS knowledge, Microsoft 365 proficiency, Active Directory experience, networking and security knowledge, and strong communication and problem-solving skills.

Key Responsibilities

• troubleshooting systems
• managing inboxes
• mentoring specialists

Skills & Tools

Windows, macOS, Linux, Microsoft 365, Microsoft Teams, Microsoft OneDrive, Microsoft Outlook, Active Directory, Group Policy, VPN, Wi-Fi

Job Details

• Category: Information Technology
• Seniority: Mid Level
• Commitment: Full Time
• Workplace: Remote — Washington, District of Columbia, United States
• Salary: USD 70,000 – 85,000 / year
• Languages: English

About CharacterStrong

A technology education company providing social-emotional learning curricula and professional development for schools. — Industry: Education