B2B Sales AI Evaluation Expert

About OpenTrain

OpenTrain AI is the hiring and contracting organization for this role. OpenTrain is the #1 platform for finding and building careers in AI training and data labeling, helping contributors discover projects, build a professional profile, and apply in minutes.

Creating an OpenTrain account is free, and your profile can help showcase credible AI training experience as you grow your freelance career.

About AI Training Work

AI training is the human side of building artificial intelligence. People with professional expertise create examples, write prompts, review model outputs, and evaluate responses so AI systems can become more accurate, useful, and reliable.

In this project, your B2B sales knowledge will help shape how AI models understand discovery, qualification, solution selling, buyer engagement, proposals, and deal progression.

The Role

OpenTrain AI is recruiting a B2B Sales AI Evaluation Expert to create and refine training and evaluation data for frontier AI models. You will translate real-world business-to-business sales expertise into practical tasks that test complex sales work.

The role is suited to an experienced, quota-carrying B2B Account Executive who can produce technically accurate scenarios, realistic buyer-seller interactions, and gold-standard solutions. This is a remote contractor opportunity available worldwide, with a commitment of 20+ hours per week.

• Contractor position
• Part-time engagement requiring 20+ hours per week
• Worldwide availability
• English-language work
• Text generation and evaluation-rating tasks

What You'll Do

You will produce expert-level B2B sales tasks and reference solutions that meet defined quality standards. Your work will combine practical sales judgment with structured evaluation of AI-generated content.

You will review sales inputs and collateral, identify deal risks or gaps, verify that scenarios are practical and solvable, and refine task designs based on calibration feedback and senior review.

• Author scenarios covering discovery, lead qualification, buyer engagement, and deal progression
• Create solution-selling frameworks, business cases, proposals, and structured sales prompts
• Develop realistic buyer-seller interactions and gold-standard reference solutions
• Apply grading rubrics and evaluation frameworks to assess realism, consistency, accuracy, and model performance
• Identify customer pain points, deal risks, gaps, and effective sales pathways
• Incorporate calibration feedback while maintaining narrative and technical accuracy

Required Experience and Skills

Applicants should have approximately 3 to 8 years of experience as a quota-carrying B2B Account Executive, with hands-on experience managing discovery, lead qualification, buyer engagement, and complex deal execution. A bachelor's degree or equivalent practical experience is appropriate.

You should be comfortable producing realistic sales content and applying structured evaluation criteria. Previous experience in AI evaluation, data annotation, content review, quality assurance, or another analytical setting is helpful but not required.

• Quota-carrying B2B Account Executive experience and practical deal-execution judgment
• Expertise in discovery, lead qualification, buyer engagement, and solution selling
• Fluency with modern CRM platforms such as Salesforce or HubSpot
• Working knowledge of MEDDPICC, SPIN Selling, Challenger, or comparable methods
• Ability to create realistic sales scenarios, proposals, buyer interactions, and gold-standard solutions
• Strong written communication for sales prompts, discovery plans, qualification frameworks, proposals, and evaluation rubrics
• Ability to identify customer pain points, assess deal risk, and map effective sales pathways
• Ability to work independently, incorporate feedback, and maintain accuracy

Who Should Apply

This opportunity is a strong fit for a B2B sales professional who wants to apply practical Account Executive experience to cutting-edge AI development. You should be able to distinguish realistic, strategically sound sales work from vague or impractical responses.

You do not need previous AI training or data-labeling experience, but you should bring strong domain judgment, clear writing, and the ability to evaluate complex sales situations consistently.

• Experienced B2B Account Executives with complex sales experience
• Sales professionals familiar with CRM workflows and qualification methodologies
• Independent contributors who can follow detailed guidelines and respond to review
• Experts interested in flexible, remote work shaping how AI models perform in business contexts

Why Work With OpenTrain

AI training and data-labeling work is a fast-growing part of the technology industry, and specialized expertise is especially valuable. Contributors help influence how modern AI systems understand professional situations and generate useful responses.

OpenTrain gives you a place to build a lasting AI training portfolio, discover projects aligned with your skills, and demonstrate credible experience as you grow in this field.

• Remote work available worldwide
• Flexible contractor opportunity for 20+ hours per week
• Apply professional B2B sales expertise to frontier AI evaluation
• Build experience in AI training, text generation, and model evaluation