Software Support & Training Specialist

Five Star Technology Solutions; United States; On-site; USD 55,000 - 75,000; Full time

Job summary

Five Star Technology Solutions is seeking a Software Support & Training Specialist to provide high-quality technical support for our software clients and to design and deliver training for school districts.

This role blends ticket-based troubleshooting with proactive client education, requiring strong communication with district staff and occasional travel for training events and the annual conference.

Qualifications

• Experience working with Excel data files (CSV) and data manipulation (sorting, filtering, formulas).
• Background in technical support/help desk environments.
• Experience delivering training in K-12 settings preferred.
• Experience with Google Apps (Gmail, Drive, Docs, Sheets, Looker Studio).
• Excellent written and verbal communication skills in person, on the phone, and virtual.
• Ability to present confidently on the company's software solutions.

Responsibilities

• Provide technical support via ticketing system, phone, and email.
• Work with district staff to resolve issues in a timely, process-driven manner.
• Access client data, troubleshoot data file imports, and QA software solutions.
• Maintain records of work and communication with districts; relay client feedback for product improvements.
• Escalate issues to higher-level support until resolved.

Skills

Excel data manipulation

Technical support

Training delivery

Google Apps

Communication

Presentation

Remote work

Self-motivation

Problem solving

Job description

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