Technical Support & Customer Success Analyst – AI Workflow Evaluation | $55/hr Remote

Crossing Hurdles is seeking a Customer Support Expert to enhance their customer support operations. The role involves designing structured customer support scenarios, managing ticket handling, and evaluating AI-generated responses against defined support standards.

Responsibilities:

• Design structured customer support scenarios with deterministic evaluation rubrics
• Create tasks involving ticket handling, macro selection, and knowledge base usage
• Develop exception management scenarios including refunds, escalations, and policy enforcement
• Build content operations tasks such as knowledge base article creation and validation
• Ensure all outputs are based on verifiable rules and correct resolutions
• Evaluate AI-generated responses against defined support standards

Requirements:

• Strong experience in customer support or customer experience operations
• Strong expertise with support platforms such as Zendesk, Intercom, or similar
• Strong experience with macros, automation, or knowledge base content
• Ability to create and evaluate support artifacts such as ticket responses and escalation notes
• Strong written communication with clear, structured reasoning
• Strong attention to detail and problem-solving skills
• Ability to work independently and manage complex support scenarios efficiently