Customer Support, Customer Success & Billing Operations | AI Evaluation & Quality Assurance

About the Project

Truelancer AI is seeking experienced B2B SaaS Customer Support, Customer Success, and Billing Operations professionals to contribute to an advanced AI evaluation and quality assurance project.

The project requires hands-on domain experts to evaluate complex enterprise AI tasks, multi-step operational workflows, task resolution quality, and grading rubrics across interconnected SaaS platforms.

As a Customer Support, Success & Billing Operations Domain Expert, you will serve as a ground-truth Quality Assurance (QA) authority, ensuring that AI-generated outputs, workflow resolutions, and operational recommendations reflect authentic enterprise practices, policy compliance, technical accuracy, and real-world SaaS operational standards.

The ideal candidate will have at least 5+ years of direct, hands-on post-sales operational experience in a B2B SaaS environment, with specialised expertise in one or more of the following areas:

• Tier 2/3 Technical Customer Support.
• Senior Enterprise Customer Success Management.
• Customer Success Operations (CS Ops), Customer Health & Adoption.
• Subscription Billing Support and Revenue Operations.

Key Responsibilities

• Perform ground-truth QA and audit complex, multi-step AI-generated enterprise workflows for accuracy, operational quality, policy compliance, and real-world applicability.
• Evaluate AI-generated customer support resolutions, technical troubleshooting steps, customer success recommendations, and subscription billing workflows.
• Review and validate AI-generated prompts and task scenarios to ensure they reflect authentic, realistic enterprise SaaS challenges rather than synthetic or generic assumptions.
• Validate, author, and calibrate evaluation and grading rubrics for assessing task completion, workflow accuracy, policy adherence, and overall resolution quality.
• Audit multi-application enterprise workflows by cross-referencing and reconciling conflicting information across three or more business platforms simultaneously.
• Evaluate Tier 2/3 technical support workflows, including ticket management, issue triage, bug reproduction, technical troubleshooting, and engineering escalations.
• Assess Customer Success Management workflows, including enterprise account management, customer renewals, Quarterly Business Reviews (QBRs), churn mitigation, and executive sponsor relationships.
• Evaluate Customer Success Operations processes, including customer health scoring, retention modelling, product adoption, customer utilisation, and performance reporting.
• Review subscription billing operations, including invoice disputes, dunning management, failed payment resolution, refund requests, and billing policy compliance.
• Assess AI-generated recommendations and actions for adherence to established business policies, contractual obligations, and operational approval requirements.
• Identify and flag unauthorised refunds, credits, contract repricing, data or access-control (ACL) leaks, and unapproved external communications.
• Evaluate workflows involving customer support, customer success, subscription management, and revenue operations across interconnected SaaS platforms.
• Identify inconsistencies, incorrect resolutions, missing operational context, policy violations, and technically impractical recommendations in AI-generated outputs.
• Provide structured, actionable expert feedback to improve AI model responses, workflow execution, and evaluation frameworks.
• Assess the accuracy, contextual relevance, technical soundness, and operational feasibility of AI-generated task outcomes.

Mandatory Requirements

• 5+ years of direct, hands-on post-sales operational experience in a B2B SaaS environment.

• Proven professional background in at least one of the following specialised roles:

  • Tier 2/3 Technical Support Engineer: Experience owning end-to-end ticket management, issue triage, bug reproduction, technical troubleshooting, and engineering escalations.
  • Senior Enterprise Customer Success Manager (CSM): Experience managing enterprise accounts, customer renewals, QBRs, churn mitigation, and executive sponsor relationships.
  • Customer Success Operations (CS Ops) / Health & Adoption Lead: Experience managing customer health scoring, retention modelling, product adoption, and utilisation reporting.
  • Subscription Billing Support Lead: Experience handling invoice disputes, dunning processes, failed payments, refund policies, and subscription billing operations using Stripe or equivalent platforms.

• Hands-on proficiency with enterprise SaaS platforms and operational tools, including:

  • Customer Support: Intercom, Zendesk.
  • CRM & Customer Management: Salesforce, HubSpot.
  • Subscription Billing: Stripe, Chargebee, Zuora.
  • Customer Analytics & Reporting: Metabase, Looker, Gainsight.
  • Collaboration & Documentation: Slack, Notion, Google Workspace, and Microsoft Office.

• Demonstrated ability to audit complex, multi-step enterprise workflows by cross-referencing and reconciling conflicting data across three or more business platforms simultaneously.

• Strong understanding of enterprise support, customer success, subscription billing, and revenue operations workflows.

• Ability to evaluate operational policies and grading rubrics, identifying unauthorised refunds, credits, contract repricing, data or access-control (ACL) leaks, and unapproved external communications.

• Proven ability to develop, validate, and assess authentic, non-synthetic task scenarios and prompts based on real-world enterprise SaaS challenges.

• Strong understanding of customer lifecycle management, customer retention, renewals, product adoption, and customer health monitoring.

• Hands-on experience with ticketing systems, customer account management, billing operations, and cross-functional workflow coordination.

• Excellent analytical, problem-solving, and critical-thinking skills, with the ability to identify discrepancies across multiple systems and evaluate the correctness of AI-generated resolutions.

• Strong written communication skills and the ability to provide clear, structured, and actionable feedback on AI-generated outputs.

• Bachelor's degree in Business, Information Systems, Computer Science, or a related discipline, or equivalent practical industry experience.

Preferred Qualifications

• Experience evaluating, training, or assessing AI tools and Large Language Models (LLMs) on domain-specific enterprise tasks.
• Experience designing, authoring, or calibrating AI evaluation rubrics and quality assessment frameworks.
• Background in establishing or managing cross-functional workflows across Customer Support, Customer Success, and Revenue Operations teams.
• Deep familiarity with REST APIs, webhooks, and technical integration troubleshooting within SaaS products.
• Experience evaluating complex, multi-application enterprise workflows and AI-generated operational decisions.
• Experience working with enterprise SaaS ecosystems involving interconnected CRM, support, billing, analytics, and customer success platforms.

Ideal Candidate Profile

We are looking for experienced B2B SaaS Customer Support, Customer Success, and Billing Operations professionals who have directly managed or influenced post-sales operational workflows and can apply their practical industry knowledge to evaluate AI-generated tasks and outcomes.

The ideal candidate should be able to distinguish between:

• Generic versus authentic enterprise SaaS operational workflows.
• Theoretical troubleshooting recommendations versus technically accurate and actionable resolutions.
• Correct versus incorrect customer support ticket triage and engineering escalations.
• Effective versus ineffective customer success and retention strategies.
• Accurate versus inconsistent customer health scoring and product adoption reporting.
• Compliant versus unauthorised billing actions, refunds, credits, and contract modifications.
• Consistent versus conflicting information across multiple interconnected SaaS platforms.
• Appropriate versus unauthorised external communications and data access.
• AI-generated responses that merely sound professional versus outputs that reflect genuine hands-on enterprise operational expertise.

Candidates should demonstrate strong technical understanding, operational judgement, analytical ability, policy awareness, and problem-solving skills, along with the ability to identify workflow gaps, validate task outcomes, and provide structured, actionable feedback to improve AI systems.

Engagement Details

• Engagement Type: 1099 Contract – Project-based / Freelance
• Work Mode: Remote
• Domain: Customer Support, Customer Success & Billing Operations | AI Evaluation & Quality Assurance
• Experience Required: 5+ Years
• Seniority: Experienced / Senior-Level B2B SaaS Operations Professionals
• Opportunity: Apply real-world B2B SaaS operational expertise to the evaluation, validation, and quality improvement of advanced AI systems and enterprise workflows.

Screening & Qualification Details

• Berribot AI Interview (Assigned, Completed, Not responding, Link not received, Issue)
• AI Berribot Assessment Result (Pass, Fail)
• Client Interview (Yet to be scheduled, Scheduled, Completed, Backout)
• Client Interview result (Pass, Fail)
• US work authorization status (US Citizen, US Green Card Holder (Permanent Resident), US Visa Holder (e.g., H-1B, H-4 EAD, F-1 OPT, F-1 STEM OPT, etc.), Others)