Software Support & Training Specialist

The Software Support & Training Specialist provides high-quality technical support to Five Star's software clients and designs and delivers training to help school districts get the most out of Five Star's software products. This role blends day-to-day ticket-based troubleshooting with proactive client education, fielding support requests one day and leading a training session the next. Strong communication skills are essential for building healthy working relationships with district staff, including technical staff, teachers, and administrators.
The Software Support & Training Specialist will work remotely and report to our Head of Service Operations. Essential Functions

• Software Support
• Provide technical support services via a ticketing system, phone, and email
• Work closely with school district personnel and team members to ensure timely, process-driven resolution of issues
• Access client assessment data from vendor sites and import files into Pivot; troubleshoot data file import issues on a client-by-client basis
• Participate in quality assurance testing of software solutions
• Maintain accurate records of work completed and communication with districts
• Relay feedback received during client interactions to inform product enhancements
• Escalate issues to higher-level support when necessary, collaborating until problems are fully resolved

Training & Engagement

• Schedule and conduct training sessions for clients as needed, in varied delivery methods (synchronous onsite, synchronous virtual, and asynchronous)
• Collaborate on the development and distribution of software training and engagement materials for improved client communication
• Proactively engage with key client contacts to build and maintain relationships and identify client needs
• Monitor client service tickets and usage analytics to identify clients who need additional training or are at risk for low engagement
• Report and track the effectiveness of training sessions and events
• Lead and interact with participants in on-site and virtual workshops at multiple skill levels

Requirements & Preferences

• Previous experience working with data files from Microsoft Excel, including CSV files, and data manipulation (sorting, filtering, formulas)
• Previous experience working in a technical support/help desk environment is preferred
• Previous experience delivering training or professional development, ideally in a K-12 setting, is preferred
• Experience with Google Apps (Gmail, Drive, Docs, Sheets, Looker Studio) preferred
• Excellent written and verbal communication skills, in person, on the phone, and in virtual settings
• Ability to present confidently and competently on the company's software solutions
• Self-motivated with a commitment to total customer satisfaction and a positive, team-oriented attitude
• Strong problem-solving and critical-thinking skills; ability to learn quickly and meet deadlines
• Ability to primarily work remotely with occasional travel for training events and the annual conference