Technical Support Specialist (L2)

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 SSO/SAML authentication issues between district identity providers (Clever, ClassLink, Google Workspace for Education, Azure AD/Entra ID, ADFS, Okta) and CharacterStrong's platform.
  • Diagnose and resolve rostering and Student Information System (SIS) integration issues — sync failures, data mismatches, provisioning errors — across platforms such as PowerSchool, Infinite Campus, Skyward, and OneRoster/Ed-Fi–based feeds.
  • Troubleshoot and resolve advanced technical issues related to operating systems (Windows, macOS, Linux, ChromeOS), user accounts, permissions, and device configurations in K-12 environments.
  • Support enterprise/education applications including Microsoft 365 and Google Workspace for Education.
  • Understand and apply student data privacy requirements (FERPA, COPPA, state-level student privacy laws) in day-to-day support decisions.
  • Assist with network connectivity issues, including VPN, Wi-Fi, and district firewall/content-filter interactions that affect access to CharacterStrong's platform.
  • Document troubleshooting steps, resolutions, and knowledge-base articles for recurring issues — especially SIS/SSO integration patterns specific to different districts and vendors.
  • 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/district 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

• • Perform other duties as assigned.

Required Qualifications

• 3-4 years of experience in a technical support role within a K-12 school district, edtech company, or educational institution IT department (not generalist corporate helpdesk).
• Hands-on experience with at least one major SIS platform (PowerSchool, Infinite Campus, Skyward, or similar) — provisioning, data exports, sync troubleshooting.
• Working knowledge of SSO/SAML, OAuth, and education rostering standards (Clever, ClassLink, OneRoster, Ed-Fi) and the ability to troubleshoot authentication failures between an identity provider and a third-party application.
• Understanding of student data privacy obligations (FERPA, COPPA) and how they shape support practices.
• Strong knowledge of Windows and macOS operating systems; familiarity with ChromeOS is a plus given its prevalence in K-12.
• Proficiency with Microsoft 365 and/or Google Workspace for Education.
• Excellent analytical and problem-solving skills, particularly in diagnosing integration issues across systems you don't control end-to-end (a district's identity provider, a third-party SIS, and your own platform).
• Strong verbal and written communication abilities — comfortable explaining technical root causes to non-technical school staff (teachers, counselors, IT directors).
• 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!