B2B Sales AI Evaluation Expert

About OpenTrain

OpenTrain is the #1 platform for building careers in AI training and data labeling. We connect skilled contributors with specialized, remote projects where they can grow a durable freelance career working on the human side of AI.

We focus on helping people discover projects, build a consistent portfolio, and take on higher-value evaluation and annotation work in a fast-growing industry.

About AI training and this work

AI training (also called data labeling or human feedback) is how modern models learn from examples and human judgment. Evaluators design criteria, score model outputs, and provide written justifications so models improve reliably and safely.

This role sits at the intersection of sales expertise and AI evaluation: your real-world B2B sales experience will shape how models are judged on practical sales deliverables.

The Role

You will evaluate AI-generated and human-created B2B sales artifacts using task-specific grading rubrics and produce robust, evidence-based justifications so scores are reproducible and defensible. Work is remote and contract-based, supporting training of generative and evaluation systems.

• Design precise grading criteria for B2B sales deliverables
• Score samples such as prospecting sequences, outreach emails, discovery/demo plans, account plans, proposals, mutual action plans, and pipeline/forecast reviews
• Provide clear, written justifications that explain each score and can withstand peer calibration

What You'll Do

Day-to-day you will build and refine rubrics, assess model and human outputs against those rubrics, respond to calibration feedback from senior reviewers, and ensure consistency across evaluation cases.

• Create and refine task-specific grading rubrics for varied sales artifacts
• Score AI-generated and human work samples against established criteria
• Write concise, evidence-based rationales for each score
• Incorporate structured feedback from senior reviewers and iterate quickly
• Maintain consistent judgment across outputs and participate in peer calibration

Requirements

We need experienced sales professionals who can translate real-world selling know-how into repeatable evaluation standards. Your written explanations must be clear, defensible, and detail-oriented.

• 5+ years of professional B2B sales experience, including quota-carrying roles
• Background as an Account Executive or Sales Development Representative selling into large enterprises
• Deep fluency in outbound prospecting, sequencing, discovery, qualification, deal management, pipeline hygiene, forecasting, and structured sales methodologies
• Strong written communication and sound judgment for explaining evaluation decisions
• Detail-oriented, consistent, and comfortable with peer review and calibration
• Prior experience with AI training, evaluation, or human-data projects is a strong plus
• Fluent English required

Compensation & Commitment

This is a remote contractor role with competitive hourly pay and a flexible but committed schedule.

• Pay: USD $100 to $150 per hour
• Default commitment: 40 hours per week; time requirement listed as 20+ hours/week
• Employment type: Contractor, Part-time
• Worldwide applicants welcome (remote)

How It Works / How To Apply

If you meet the experience requirements, you'll apply through OpenTrain and complete any onboarding and calibration tasks required for this project. Expect to participate in rubric calibration and sample scoring before full assignment.

OpenTrain supports your freelance career growth in AI training—this role offers the chance to shape how sales-oriented AI systems perform in real-world B2B workflows.

• Apply with your sales background and relevant examples of work or outcomes (quota attainment, territory size, deal complexity)
• Be prepared to complete evaluation samples and calibration exercises as part of onboarding
• Successful applicants will be invited to ongoing scoring work and reviewer calibration sessions