Technical Support Specialist

What You’ll Do

Own the Customer Support Experience: Be the first technical responder for incoming district tickets — diagnose, triage, and resolve issues directly with district staff over phone, email, and screenshare. Train customers on system behavior, walk them through configuration steps, and turn one-off support interactions into knowledge that scales.

Diagnose and Resolve Production Issues: Investigate complex production issues application logs, database records, integration processes, and deployed hardware. Perform root-cause analysis on system failures, data inconsistencies, and integration errors.

Support SIS Integrations: Troubleshoot data synchronization and sync failures

Diagnose REST API errors and validate roster and data accuracy.

Investigate Production Data: Query Oracle production databases using SQL and PL/SQL to investigate data issues, validate records, and support data corrections. Reason about root cause across schemas, integrations, and the legacy and modern application boundaries.

Support Deployed Hardware: Troubleshoot check-in kiosks, ID card printers, badge readers, and barcode scanners deployed across school environments. Diagnose connectivity, network configuration, and device-server communication issues alongside district IT teams.

Configure School Systems: Support district-level configuration of school calendars, bell schedules, attendance notification workflows, tardy alerts, visitor sign-in workflows, and kiosk behaviors. Assist in onboarding and configuring new districts.

Build the Knowledge Base: Author and maintain runbooks, troubleshooting guides, and configuration documentation. Documentation contribution is a core deliverable — much of the team’s institutional knowledge has lived in heads rather than docs, and this role is one of the people changing that.

Collaborate Cross-Functionally: Work with Engineering, Implementation, Customer Support, and district IT to escalate, diagnose, and resolve issues. Translate complex technical findings into clear, actionable resolution plans.

Day-to-Day Breakdown

• 55% direct ticket work — investigating and resolving district support requests
• 20% authoring and refining documentation, runbooks, and knowledge-base content
• 15% deeper investigation and escalation work on complex production issues
• 10% supporting district setup, onboarding, and configuration changes

Requirements

Technical Skills

• SQL (production-database depth): Strong SQL skills with demonstrated experience investigating production data, joining across schemas, hunting anomalies, and analyzing application logs. Oracle experience preferred.
• REST API Integration Troubleshooting: Experience diagnosing integration failures, debugging payloads, validating data transfer between systems, and reasoning about retry/idempotency behavior.
• Programming for Debugging: Working knowledge of at least one language (Python, Java, C#, JavaScript) at the level of reading code, interpreting stack traces, and analyzing system logs. Full development experience is not required; debugging fluency is.
• Hardware and Networking Fundamentals: Comfortable troubleshooting deployed devices, basic networking concepts (firewalls, ports, NAT, DNS), and district-network environments. Direct experience with kiosks, scanners, or similar hardware is a strong plus.
• Customer-Facing Troubleshooting: Experience resolving issues live with end users — phone, screenshare, email — in a way that builds confidence rather than friction.
• Enterprise Application Support: Experience supporting enterprise applications in production environments — you understand what production-grade reliability requires.
• Tools: Proficient in Jira (ticket triage, queue ownership, escalation workflows) and Confluence (documentation authoring, KB structure).

Soft Skills

• Customer Orientation:
• Curiosity and Problem-Solving:
• Comfort with Ambiguity:
• Clear Communicator:
• Documentation Discipline:
• Cross-Functional Collaboration:

Desired Experience

• Bachelor’s degree in computer science, information systems, or related field (or equivalent practical experience).
• 4+ years of experience in technical support, production support, or similar roles in an enterprise software environment.
• 2+ years of hands-on experience querying production databases.
• Direct experience with EdTech platforms is a strong plus — prior exposure to LMS, SIS, or adjacent education-software systems particularly valued.

Other Requirements

• Excellent written and verbal English — phone-level fluency required. This role involves direct customer interaction, including live troubleshooting calls with district staff.
• Able to work aligned with Eastern Time (EST).

Nice to Have

• Hands-on Oracle PL/SQL experience (stored procedures, packages, query optimization)
• Familiarity with Windows Server, IIS, or similar legacy hosting environments
• Experience supporting .NET-based applications in production
• Interest in integrating AI tools (Claude, Copilot, Rovo) to simplify support workflows and accelerate documentation
• Direct experience with K–12 SIS integrations (PowerSchool, Infinite Campus, Skyward, eSchoolData)
• Experience with SCORM, xAPI, LTI, or SSO/SAML troubleshooting