Stripe Payment Operations AI Training Specialist

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. It helps people discover projects, build a professional profile, and apply to work that matches their experience. Creating an OpenTrain account is free.

OpenTrain AI is hiring and contracting for this remote, part-time opportunity.

About AI Training Work

AI training is the human work behind modern artificial intelligence. Contributors complete realistic tasks, prepare examples, write instructions, and evaluate results so AI systems can learn how people handle practical problems.

This role focuses on payment and financial operations workflows. Your demonstrations, documentation, prompts, rubrics, and quality reviews will help create useful training data for AI development.

The Role

As a Stripe Payment Operations AI Training Specialist, you will complete and document realistic workflows in Stripe according to detailed project instructions. You will explain the actions taken, record screen-based demonstrations, and review completed work against defined quality standards.

This is independent remote contractor work for an intermediate-level professional. The expected time commitment is 20 or more hours per week, and the listed compensation is $90 to $170 USD per hour.

• Contractor and part-time engagement
• Remote work
• 20+ hours per week
• English-language work
• Listed compensation: $90-$170 USD per hour

What You’ll Do

You will use your hands-on Stripe knowledge to carry out payment and financial operations tasks, explain the workflow clearly, and turn completed work into structured AI training materials.

• Complete assigned Stripe workflows using detailed instructions
• Navigate customers, payments, invoices, subscriptions, refunds, disputes, transactions, and related records
• Record your screen while demonstrating workflow steps and relevant Stripe features
• Appear on camera while explaining workflows
• Create realistic prompts and detailed rubrics based on completed workflows
• Document processes clearly and review tasks for accuracy and project alignment

Required Experience and Skills

You should have strong practical Stripe experience from a professional setting such as finance, payments, SaaS, e-commerce, or a related field. You must be able to access Stripe currently, navigate it independently, and communicate workflow decisions clearly.

Prior experience with human-data annotation, labeling, RLHF, AI response evaluation, or model evaluation is valuable but is not presented as a substitute for the required Stripe and financial operations experience.

• Hands-on experience managing Stripe customers, payments, invoices, subscriptions, refunds, disputes, and transactions
• Practical knowledge of payment processing, billing, subscriptions, invoicing, refunds, disputes, or financial operations
• Current access to Stripe and the ability to work independently in the platform
• Ability to explain workflow steps clearly in writing and verbally
• Ability to create realistic prompts and detailed rubrics
• Comfort recording and sharing your screen, including appearing on camera
• Strong attention to detail and clear communication

Helpful Background

Experience with AI training or human-generated data can help you succeed in the workflow documentation and evaluation portions of the role. Familiarity with Stripe Billing, reporting, and other Stripe features is also useful.

• Data annotation or labeling
• Reinforcement learning from human feedback
• AI response or model evaluation
• Stripe Billing and reporting

Why Build Your AI Training Career With OpenTrain

AI training and data-labeling work is a growing way to participate in technology without leaving your professional specialty behind. OpenTrain helps you build a profile that showcases credible project experience and supports a longer-term career in AI training.

Apply through OpenTrain to put your Stripe operations knowledge toward practical AI development work while working remotely and independently.

• Work remotely with flexible contractor scheduling
• Apply your existing payment operations expertise to AI development
• Build a profile that reflects your AI training experience
• Create a foundation for future opportunities in a fast-growing field