Customer Support Specialist

Overview of the Role:

The Customer Support Specialist (CSS) provides frontline technical support for Upshop customers across our retail software platforms. As a primary point of contact through phone and the support ticketing system, the CSS investigates application, configuration, data, connectivity, and in-store environment issues; resolves problems using established procedures and available knowledge; and maintains clear customer communication throughout the ticket lifecycle. The CSS is expected to think critically, take ownership, use approved AI and knowledge tools responsibly, and prepare complete evidence-based escalations when deeper investigation is required.

This role builds technical expertise over time and contributes to stronger first-contact resolution and customer self-service.

Key Responsibilities:

• Software Troubleshooting: Diagnose and resolve common application, configuration, access, data, and workflow issues using established support procedures and technical resources.
• Installation & Environment Support: Assist with supported software installation, maintenance, connectivity, and in-store peripheral troubleshooting, including printers, scales, scanners, and other supported devices.
• Customer Assistance: Serve as a primary customer contact by phone and through support tickets, responding promptly and communicating clearly and professionally.
• First-Contact Resolution: Investigate and resolve issues at the earliest appropriate point, applying sound judgment and recognizing when additional technical expertise is needed.
• Ticket Ownership & SLAs: Maintain accurate case records, customer updates, troubleshooting steps, next actions, and resolutions; manage assigned tickets against service expectations and escalation procedures.
• Knowledge & Documentation: Use and contribute to approved knowledge articles and troubleshooting guides, documenting repeatable fixes and identifying opportunities for customer self-service.
• Product Knowledge: Develop working knowledge of Upshop applications, retail workflows, and common customer issues; provide accurate guidance within established areas of expertise.
• Escalation Preparation: Gather relevant logs, screenshots, configuration details, data samples, reproduction steps, business impact, and actions already attempted before escalating complex issues to CSS II or other appropriate teams.
• On-Call & Coverage: Participate in scheduled coverage or on-call responsibilities as assigned based on the team operating model.
• Customer Communication & Prioritization: Communicate empathetically and effectively with customers and colleagues; prioritize competing tickets and provide timely, meaningful status updates.
• Continuous Learning: Build proficiency in software systems, APIs, data concepts, hardware, network connectivity, and retail operations through training, coaching, and hands-on support work.
• AI-Assisted Support & Additional Duties: Use company-approved AI tools to support troubleshooting, research, and documentation while following customer data and security requirements. Perform other related duties and projects as assigned.

Required Qualifications

• Proven experience in customer or technical support (software/IT preferred).
• Strong analytical, problem-solving, and troubleshooting skills.
• Ability to follow documented troubleshooting processes, communicate by phone, and document investigations clearly.
• Exceptional critical thinking skills, ability to focus under pressure.
• Ability to manage multiple tasks and prioritize effectively in a fast-paced environment.
• Excellent verbal and written communication skills with a customer-first mentality and empathy in responses.
• Works independently and collaborates effectively in a team.
• Working knowledge of software…