Sales AI Task Designer (Remote Contractor)

About OpenTrain

OpenTrain is the #1 platform for people building careers in AI training and data labeling. It helps freelancers discover AI training projects, consolidate opportunities, and build a unified portfolio — making it easier to grow a durable freelance career in the human side of AI.

Why AI training matters

AI training (data labeling and human feedback work) is how modern AI systems learn from examples prepared and reviewed by people. Contributors write prompts, evaluate model outputs, design tasks, and rate performance — work that’s remote, flexible, and central to how AI behaves in the real world.

The role

OpenTrain is recruiting for a contractor to design sales workflow tasks used to evaluate AI agents. You will analyze authentic workplace communications (Slack, email, internal files) and convert fragmented context into clear, realistic, multi-step scenarios and evaluation rubrics.

• Commitment: 20+ hours/week (part-time contractor)
• Workplace: Fully remote, open to candidates worldwide
• Pay: Paid hourly, $20–$45 per hour (project lists an hourly rate up to $45/hr)

What you'll do

• Review workplace communications and documents to identify decisions, actions, dependencies, and unresolved issues
• Turn fragmented information into coherent, realistic tasks for evaluating AI agents
• Create prompts and clear evaluation rubrics grounded in sales and operations contexts
• Synthesize details across conversations and documents into multi-step scenarios
• Provide nuanced explanations and detailed feedback on task design and context
• Handle confidential and sensitive business information with discretion and professionalism

Requirements

You must have demonstrable, relevant experience and strong communication abilities. The project relies on judgment, analytical thinking, and the ability to resolve ambiguity across timelines and data types.

• Proven experience in sales, operations, or a related startup environment
• Strong written and verbal communication skills (English required)
• Ability to trace dependencies and resolve ambiguity across timelines and data types
• Experience improving processes in evolving business settings
• Strong critical thinking, analytical, and problem-solving skills
• Demonstrated discretion and professionalism when working with confidential information

Helpful background

• Experience working with messy workplace communications and internal documentation
• Familiarity with sales workflows, startup operations, or related business process work

How the work is structured

This is a contract, part-time role. Tasks are text-focused (data type: text) and involve creating and evaluating prompts, question-answer items, ratings, and RLHF-style evaluation. The project uses the client’s chosen tools (). Language of work: English.

• Labeling / evaluation types include: TEXT_GENERATION, QUESTION_ANSWERING, EVALUATION_RATING, RLHF
• Employment types: Contractor, Part-time
• Worldwide candidates may apply

How to apply

Create a free OpenTrain account, complete your profile, and submit your application to this posting. Highlight relevant sales or operations experience, examples of working with internal communications, and any prior task-design or evaluation work.