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Posted Jun 7, 2026

Customer Support Specialist, AI Response Evaluation

Job Description: • Reviewing AI-generated customer support responses for accuracy, clarity, and helpfulness • Evaluating tone, empathy, and professionalism in customer interactions • Identifying poor support behaviors (e.g., dismissiveness, lack of resolution, incorrect guidance) • Assessing whether AI responses appropriately address customer intent and resolve issues • Evaluating how AI handles frustration, confusion, or escalating user behavior • Identifying gaps in responses, including missing steps, unclear instructions, or lack of follow-through • Detecting overconfident, misleading, or incorrect responses • Evaluating multi-turn conversations for consistency, escalation handling, and resolution quality • Identifying patterns of agreement without problem-solving (e.g., empty empathy or unhelpful reassurance) • Participating in or reviewing red teaming exercises to surface failure modes in support scenarios • Supporting quality assurance (QA) to ensure consistency across evaluations • Documenting edge cases, failure patterns, and customer experience risks • Providing structured written feedback to internal teams • Collaborating with interdisciplinary teams on AI quality, safety, and evaluation frameworks • Maintaining strict confidentiality and quality standards. Requirements: • Successful candidates are detail-oriented, customer-focused, and experienced in evaluating or delivering high-quality support in fast-paced environments. • Professional experience in one or more of the following: Customer support (chat, email, or phone) • Call centers or contact centers • Technical support or help desk roles • Online support environments (SaaS, e-commerce, fintech, etc.) • Strong understanding of high-quality customer experience and service standards • Effective communication in customer-facing interactions • Common support workflows (triaging, troubleshooting, escalation) • How customers interpret and respond to support interactions • Ability to identify: • Poor or incomplete resolutions • Incorrect or misleading information • Inappropriate tone (e.g., robotic, dismissive, overly casual) • Lack of empathy or ineffective de-escalation • Failure to follow support best practices • Strong written communication skills and ability to clearly explain reasoning. • Experience with or interest in: • Evaluating conversations or QA for support teams • Working with AI tools, chatbots, or automated systems • Assessing how systems perform under real customer behavior. • Comfort with: • Tech tools and platforms (Slack, spreadsheets, dashboards) • Evaluating AI-generated responses (no coding required, but must be tech-comfortable) • Ambiguity, iteration, and feedback-driven workflows. • Willingness to: • Sign NDAs and work with sensitive content. • Nice to Have (Not Required) • Experience in QA, coaching, or training within support teams • Background in trust & safety or content moderation • Experience with chatbot or AI-assisted support tools • Familiarity with CX metrics (CSAT, QA scoring, resolution rate) • Interest in AI, automation, or improving customer experience systems. Benefits: