CSS II: Complex SaaS Escalations & Root Cause

Upshop; California; On-site; USD 85,000 - 120,000; Full time

Job summary

Upshop is seeking a Customer Support Specialist II to own complex escalated tickets, tracing issues across configurations, data, and integrations. You will replicate environments, verify root causes, and prepare a robust handoff with evidence for engineering teams.

You will mentor CSS I staff, manage multiple tickets with SLAs, and contribute to playbooks. Expect on-call rotation, cross-functional collaboration, and responsible use of AI tools in investigations.

Qualifications

• 4+ years in technical or application support, SaaS multi-tenant environments.
• Strong root-cause analysis and evidence-based troubleshooting.
• Comfort reading APIs, JSON, SQL results, and logs.
• Experience with monitoring/observability tools and incident response.

Responsibilities

• Escalation ownership for Level 1 tickets and complex issues.
• Perform deep-dive investigations across configurations, data, and logs.
• Prepare clear handoff documentation with reproduction steps and impact.
• Troubleshoot in-store hardware and hybrid cloud/on-prem environments.
• Document tickets, SLAs, troubleshooting steps, and changes.
• Communicate updates to customers with empathy and clarity.
• Collaborate with product/engineering on recurring issues and releases.
• Participate in on-call rotation and incident response.
• Create knowledge base content and playbooks for the team.

Skills

Escalation ownership

Deep-dive investigation

Technical fluency

Communication

Mentoring

Queue management

Incident handling

Cross-functional collaboration

Tools

Zendesk

Jira

Azure DevOps

Postman

Job description

Upshop is seeking a Customer Support Specialist II to own complex escalated tickets, tracing issues across configurations, data, and integrations. You will replicate environments, verify root causes, and prepare a robust handoff with evidence for engineering teams.

You will mentor CSS I staff, manage multiple tickets with SLAs, and contribute to playbooks. Expect on-call rotation, cross-functional collaboration, and responsible use of AI tools in investigations.