About Upshop:

Upshop is hiring a Customer Support Specialist II (CSS II) to own our most complex customer issues, including the ones for which we don’t have a playbook yet. As the primary escalation point from Level 1 support, you will dig into production problems across Upshop's fresh retail platform and its integrations and find what went wrong: configuration, data, integrations, in-store environment, or application bugs. You will fix what support can fix, and when you cannot, you will hand engineering a clear write-up with the evidence, so they are not starting from zero. 

The work crosses systems. You will check tenant and license settings, query Cosmos/Mongo and SQL Server, review feature flags, follow logs and traces in Datadog. You will not ship features full time, but you should be able to follow code, data, and logs far enough to prove the cause. You will use AI tools every day, customer data, and you will help mentor the CSS I team. The goal is fewer bounce-backs, faster answers on tough issues, and engineering partners who trust what you send them. 

This role is for someone who enjoys complex tickets, follows the evidence, and leaves the team better than they found it. 

Key Responsibilities: 

• Escalation Ownership: Act as the primary escalation point for Level 1 support and own complex escalated tickets that need deep investigation across Upshop's product suite and integrations. 

• Deep-Dive Investigation: Trace issues through tenant and license configuration, data, integrations, feature flags, logs and traces, and product code when needed. Replicate user environments and prove the root cause rather than treating symptoms. 

• Resolution & Engineering Handoff: Resolve what support can resolve. When an issue needs engineering, send a clear package with reproduction steps, evidence, impact, and what has been ruled out, so defects move quickly without bounce-backs. 

• In-Store & Environment Support: Troubleshoot issues involving network connectivity, hybrid on-prem and cloud setups, host feeds, and in-store hardware (e.g., label printers, scales, scanners, and handheld devices). 

• Ticket Management & SLAs: Document every ticket with what is known, what has been ruled out, troubleshooting steps, resolutions, and any system changes made. Track tickets from creation through resolution and meet SLA targets. 

• Customer Communication: Write clear customer updates, manage expectations on complex or long-running issues, and deliver difficult information with empathy and professionalism. 

• Cross-functional Partnership: Partner with product and engineering on recurring issues and release-related problems, provide feedback, and suggest enhancements. 

• On-Call & Incident Support: Participate in the on-call rotation and incident response, resolving issues promptly, including outside business hours. 

• Knowledge Base & Playbooks: Create and maintain documentation, playbooks, and routing knowledge for both common and complex issues so the whole team can resolve them faster. 

• AI-Assisted Workflows: Use AI tools such as Cursor, Claude, Copilot, and in-house Agents every day to speed up investigation and cut busy work. Build and share prompts, skills, or small automations, and handle customer data responsibly when using them. 

• Mentoring: Guide CSS I team members, sharing troubleshooting techniques and best practices for customer interactions. 

• Performance Metrics & Continuous Improvement: Meet or exceed targets for response time, resolution time, and customer satisfaction, and keep improving how the team works. 

Required Qualifications: 

• Proven Experience: 4+ years of technical support, application support, or a similar role, including supporting multi-tenant SaaS and troubleshooting complex software and system issues. 

• Troubleshooting Discipline: Strong root cause analysis habits: follow the evidence, write down what you know and what has been ruled out, and decide the next steps carefully and independently. 

• Technical Fluency: Comfortable reading APIs, JSON, SQL results, and application logs. 

• Data & Platform Experience: Hands-on experience with at least two of: MongoDB/Cosmos-style databases, relational SQL (e.g., SQL Server), cloud observability (e.g., Datadog), feature flags, and Azure (or an equivalent cloud). 

• AI Tools: Hands-on experience with AI platforms such as Cursor, Claude, CoPilot, or similar. 

• Strong Communication: Clear written and verbal communication for both customers and engineers, with the ability to explain complex technical concepts to technical and non-technical audiences. 

• Escalation Handling & Mentoring: Demonstrated ability to handle escalated issues and provide technical guidance to junior team members. 

• Queue Management & Organization: Ability to manage multiple support requests and competing priorities efficiently while maintaining attention to detail and a high standard of customer service. 

Desired Skills: 

• Senior Support Experience: Prior escalation-tier or senior support experience. 

• Industry Background: Experience with retail, grocery, food service, or store operations software. 

• Automation Experience: Experience building prompts, skills, scripts, or small automations that help support work. 

• Support & Defect Tools: Familiarity with Zendesk (or similar), Jira or Azure DevOps for defect handoffs, and API tools such as Postman. 

• Incident Management: Incident work with tools like PagerDuty. 

• Hybrid & Integration Environments: Exposure to hybrid on-prem and cloud systems, host feeds, multi-tenant configuration models, and in-store hardware peripherals. 

• Certifications: CompTIA A+, ITIL, Zendesk, or related technical certifications are a plus. 

• Leadership Potential: Interest in leading technical projects or taking on leadership responsibilities within the support team.