Sales Forecasting And RevOps AI Evaluation Expert

About OpenTrain

OpenTrain is the #1 platform for finding and building careers in AI training and data labeling. We connect skilled contributors with opportunities to help develop advanced AI systems, build credible portfolios, and grow their work in a fast-expanding technology field.

About AI Evaluation Work

AI evaluation is the human side of building artificial intelligence. Specialists create realistic examples, assess model outputs, and define what accurate, useful responses should look like. In this role, your sales and revenue operations expertise will help train and evaluate AI on complex commercial decisions and workflows.

• Remote freelance contractor work
• Flexible part-time engagement of 20+ hours per week
• Directly shape how advanced AI handles sales and revenue operations problems

The Role

OpenTrain is seeking an experienced sales management, revenue operations, or sales operations specialist for a nine-week remote contractor engagement. You will create high-difficulty business scenarios, evaluation criteria, and gold-standard solutions that assess AI capabilities across sales forecasting, CRM and CPQ operations, territory and quota design, compensation planning, pipeline analytics, and related commercial strategy.

The work requires practical judgment and technical accuracy. You will help ensure that training content reflects realistic operational processes, sound commercial strategy, and precise standards for evaluating AI-generated outputs.

What You'll Do

You will develop and review text-based AI training content for sales and revenue operations use cases. Your responsibilities will include creating realistic scenarios, defining rigorous evaluation standards, reviewing peer work, and participating in calibration cycles that improve content quality and consistency.

• Create high-difficulty business scenarios for sales forecasting and revenue operations
• Write detailed evaluation criteria and gold-standard solutions
• Cover forecasting methodologies, CRM workflows, CPQ rules, territory planning, quota allocation, compensation plans, and pipeline performance
• Review and calibrate peer outputs for accuracy, consistency, and operational realism
• Validate scenarios and datasets against real-world sales and revenue operations practices
• Identify edge cases, ambiguous criteria, and gaps in evaluation rubrics
• Contribute to revision and calibration cycles that improve AI training content

Requirements

You should have substantial leadership experience in sales management, revenue operations, or sales operations. Practical fluency with Salesforce, CPQ, or HubSpot is required, along with experience analyzing complex pipeline and commercial strategy problems.

You must be able to produce executive-grade business deliverables and write clear scenarios, precise rubrics, and technically accurate gold-standard solutions. Strong attention to detail, independent judgment, and the ability to review work against exacting criteria are essential.

• Senior leadership experience in sales management, revenue operations, or sales operations
• Strong knowledge of forecasting, territory planning, quota allocation, or sales compensation design
• Practical fluency with Salesforce, CPQ, or HubSpot
• Experience with pipeline analytics and complex commercial strategy analysis
• Strong written communication and AI evaluation skills
• Ability to create realistic scenarios, gold-standard solutions, and precise rubrics
• Ability to assess outputs for accuracy, consistency, and operational realism

Helpful Background

A bachelor's degree or equivalent practical experience is welcome. Prior experience with AI evaluation, data annotation, content review, quality assurance, or related analytical work is helpful but not required.

Schedule And Engagement

This is a remote contractor engagement lasting nine weeks. The expected commitment is 20 or more hours per week, with at least four hours per day and up to 40 hours per week available. The schedule includes four hours of overlap with Pacific Time. Compensation details are not disclosed.

• Engagement type: Contractor and part-time
• Duration: 9 weeks
• Work location: Worldwide and remote
• Language: English
• Time commitment: 20+ hours per week, up to 40 hours per week
• Pacific Time overlap: 4 hours

Why Work With OpenTrain

Every major AI system depends on people who prepare examples, evaluate responses, and bring expert judgment to model development. OpenTrain helps contributors build a lasting AI training portfolio, discover opportunities aligned with their skills, and grow in a field shaping how advanced AI systems work.

• Create a profile that showcases your AI training experience
• Find opportunities matched to your professional expertise
• Build a durable portfolio in AI training and data labeling
• Work remotely with flexible hours around your schedule