Customer Support & Success Domain Expert; QA & Prompt Evaluation

Domain: Customer Support & Customer Success
Location: United States (USA)
Experience: 10+ Years
Open Positions: 7
Work Commitment: Up to 35 Hours per Week
Engagement Type: 1099 Contract - Remote | ( Freelance / Contract )
Project Nature: AI Quality Assurance, Domain Evaluation & Prompt Assessment.

Truelancer AI is looking for experienced Customer Support and Customer Success professionals to contribute to an advanced AI evaluation and quality assurance project.

The project focuses on evaluating AI-generated customer support workflows, reviewing prompts, and validating whether AI-generated outputs accurately reflect real-world enterprise customer support and success operations.

We are seeking senior professionals who have hands‑on experience managing customer interactions, resolving complex support issues, driving customer retention, handling renewals, and managing technical onboarding processes.

• Act as a domain expert and quality assurance authority for reviewing AI-generated customer support and success workflows.

• Audit multi‑step synthetic workflows and evaluate AI prompts for real‑world business authenticity.

• Review and validate AI-generated outputs against customer support and customer success best practices.

• Evaluate workflows covering:

  • Customer support ticket triage, escalation, and resolution.

  • Customer churn management and retention strategies.

  • Contract renewals and customer account management.

  • Customer usage monitoring and product adoption checks.

  • Recurring customer reporting and performance tracking.

  • Customer onboarding and implementation workflows.

  • Technical installation scheduling and coordination.

  • Billing inquiries, payment failures, and payment resolution.

• Critically evaluate and grade AI-generated outputs across different customer journeys.

• Review customer communications for authenticity, clarity, professionalism, and policy compliance.

• Validate evaluation rubrics and quality benchmarks specific to Customer Support and Customer Success.

• Identify gaps, unrealistic scenarios, and inconsistencies in AI-generated workflows.

• Provide structured feedback to improve AI model performance and output quality.

• 10+ years of professional experience in Customer Support, Customer Success, Technical Support, Customer Experience, or Technical Onboarding.

• Strong hands‑on experience managing enterprise customer support and success operations.

• Demonstrated expertise in ticket management, issue resolution, escalation handling, and customer communication.

• Experience managing customer retention, churn prevention, renewals, and product adoption.

• Understanding of customer onboarding, technical implementation, and installation coordination.

• Experience with billing operations, payment inquiries, and failed payment resolution.

• Ability to assess complex customer journeys and evaluate the quality and accuracy of operational workflows.

• Excellent analytical, critical‑thinking, and written communication skills.

• Ability to identify whether customer interactions and support scenarios are realistic and aligned with enterprise policies.

Candidates should have familiarity with customer support, CRM, payment, and analytics platforms, preferably including:

• Intercom

• Stripe

• Hub Spot

• Metabase

Experience with similar enterprise customer support and success platforms is also valuable.

We are looking to build a team of 7 domain experts with a complementary mix of experience across the following areas: