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 applications, basic hardware and network troubleshooting, and structured technical investigation. • Experience with a ticketing platform such as Zendesk (Support, Talk, or Guide), or ability to learn one quickly. • Familiarity with APIs, JSON, webhooks, or tools such as Postman; ability to collect relevant information for escalation. • Understanding of basic database and SQL concepts, including how to interpret query results and recognize data discrepancies. Desired Skills: • Experience with Zendesk, Jira, or comparable support and defect-tracking tools. • Experience supporting enterprise SaaS applications or integrated software environments. • Familiarity with structured IT troubleshooting and incident or escalation processes. • Cosmo/Mongo DB queries and concepts • Knowledge and experience with retail/ grocery concepts and terminologies • Experience with DataDog tools and concepts • Experience supporting retail/grocery operations, in-store systems, or customer-facing software platforms. • Self-directed learner who remains organized, collaborative, and customer-focused during urgent issues. • Experience using approved AI tools, technical knowledge bases, or support automation to improve efficiency.