Customer Success Ops Expert - AI Data Trainer

About OpenTrain

OpenTrain is the #1 platform for building careers in AI training and data labeling. Creating an OpenTrain account is free and gives you access to paid projects that teach AI systems how real work gets done.

We connect experienced contributors with short-term, remote contracts across the industry so you can earn on a flexible schedule while shaping how AI handles real customer scenarios.

About AI training work

AI training (also called data labeling or human feedback) is the human side of building smarter systems. Your judgments and annotations become the examples AI agents learn from—everything from support transcripts to internal notes.

Many projects let you work part time and remotely; they reward careful reasoning, clear writing, and consistent use of rubrics—the exact strengths this role requires.

The role

You will work as a Customer Success Operations evaluator (AI Data Trainer) reviewing structured B2B SaaS workplace scenarios—account notes, internal escalations, support history, and renewal context—and label whether specific information is appropriate for an AI agent to use and who should see it.

This is a remote hourly contract role with flexible scheduling, estimated at roughly 20 hours per week for about 2.5 months.

• Employment type: Contractor, Part-time.
• Schedule: Flexible, approx. 20+ hours/week.
• Duration: ~2.5 months (contract).
• Rate: USD $40.00 per hour.

What you'll do

Apply a structured rubric to many short workplace scenarios and produce labels and brief justifications. Labels are usually classification-style: yes / no / undecidable, plus a concise rationale that notes confidentiality and visibility considerations.

Work carefully through ambiguous situations—decide when internal-only notes stay hidden, when context is safe to surface, and when information is too uncertain to label. Consistency and defensible reasoning are essential.

• Label text-based scenarios (dataType: TEXT).
• Label types include CLASSIFICATION, EVALUATION_RATING, and QUESTION_ANSWERING.
• Use the provided labeling tool (OTHER) and follow project rubrics closely.
• Write short, clear justifications that demonstrate customer-confidentiality awareness.

Requirements

You must have at least 1 year of experience in Customer Success, Account Management, or Support Operations in a B2B SaaS environment and be able to apply that domain knowledge to labeling decisions.

Education: any bachelor's degree or equivalent on-the-job CS / account-management experience. You do not need to be an expert coder, but you should be comfortable reading basic technical context and making defensible judgments.

• 1+ year in Customer Success, Account Management, or Support Ops at a B2B SaaS company.
• Domain expertise in onboarding/offboarding, ticket escalation, incident communications, renewal-risk assessment, and support-history handling.
• Familiarity with CRM and ticketing tools (for example Salesforce, Gainsight, Zendesk).
• Strong English writing and careful reasoning; able to deliver short, precise justifications.
• Role-specific: strong judgment about internal-only notes vs. external-facing visibility and consistent rubric application.

Who should apply

This project fits people with hands-on B2B SaaS customer-success or support-ops experience who enjoy structured, thoughtful work and can balance nuance with fast throughput.

Applicants should be available to work remotely from one of the accepted countries and comfortable applying confidentiality-aware judgment across many short scenarios.

• Languages: English required (en).
• Accepted countries: US, CA, GB, IE, AU (not worldwide).
• Experience level: Intermediate.

Compensation, logistics & how it works

Compensation is USD $40 per hour, paid on an hourly contractor basis. Expect roughly 20 hours per week; scheduling is flexible and remote.

You'll use the project's labeling software (listed as OTHER). The work focuses on text scenarios and requires label types CLASSIFICATION, EVALUATION_RATING, and QUESTION_ANSWERING. Apply through OpenTrain—creating an account is free—and follow the project onboarding and rubric training before starting.

• Pay: $40.00 USD per hour (PAY_PER_HOUR).
• Time: ~20+ hours/week for about 2.5 months.
• Data: Text-only scenarios.
• (project will provide access and training).
• How to start: Create an OpenTrain account (free), complete any project-specific training, and begin labeling once approved.