1P Customer Support & Success Domain Expert (QA & Prompt Evaluation)

Truelancer AI; United States; Remote; USD 96,000 - 172,000; Part time

Job summary

Truelancer AI in the United States is seeking experienced Customer Support and Customer Success professionals to contribute to an advanced AI evaluation and quality assurance project focused on enterprise workflows.

You will review AI-generated prompts and outputs, audit multi-step journeys from onboarding to renewals, and provide structured feedback to improve model performance and domain fidelity across customer support, success, billing, and adoption.

Qualifications

• 10+ years of professional experience in Customer Support or Customer Success.
• Expertise in ticket management, issue resolution, and escalation handling.
• Experience with enterprise renewals, retention, and product adoption.
• Understanding of onboarding, implementation, and installation coordination.
• Strong analytical, written communication, and process evaluation skills.
• Ability to judge realism of customer journeys against enterprise policies.

Responsibilities

• Act as domain expert for reviewing AI-generated customer support workflows.
• Audit synthetic workflows and evaluate AI prompts for real-world authenticity.
• Review AI outputs against best practices in customer support and success.
• Evaluate workflows including ticket triage, escalation, renewal, onboarding, billing.
• Provide structured feedback to improve AI model outputs.
• Ensure authenticity and professionalism of customer communications.

Skills

Enterprise support

Customer retention

Ticket management

Onboarding coordination

Tools

Intercom

Stripe

HubSpot

Metabase

Job description

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.

About the Project

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.

Key Responsibilities

• 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.

Mandatory Qualifications & Skills

• 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.

Platforms & Tools

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

• Intercom

• Stripe

• HubSpot

• Metabase

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

Preferred Candidate Backgrounds

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

1. Customer Support Experts: Experienced in ticket management, customer escalations, issue resolution, and support operations.

2. Customer Success Experts: Experienced in customer retention, churn management, renewals, account management, and product adoption.

3. Technical Onboarding Experts: Experienced in customer onboarding, technical implementation, installation scheduling, and troubleshooting coordination.

Candidates with experience in AI evaluation, LLM testing, prompt engineering, or QA rubric development will have an added advantage.

Who Should Apply?

This opportunity is ideal for experienced professionals who have worked in senior roles such as:

• Director / VP of Customer Support.

• Head of Customer Success.

• Customer Support Operations Manager.

• Customer Experience (CX) Manager.

• Technical Support Manager.

• Customer Onboarding / Implementation Manager.

• Customer Success Operations Manager.

• Senior Customer Support Specialist.

Important: Candidates must have substantial hands‑on experience in real‑world enterprise customer support or success environments and be capable of evaluating AI-generated workflows from an operational perspective.