Remote B2B Sales Evaluator & Rubric Architect

Weekday 1; United States; Remote; USD 138,000 - 207,000; Full time

Job summary

Weekday 1 is seeking experienced sales professionals to join an AI evaluation initiative that improves how next-generation AI systems understand and perform real-world B2B sales work. You will define evaluation criteria and structured rubrics instead of producing sales outputs.

This remote, independent contractor role offers $100-$150 per hour with flexible hours and weekly payments. Ideal candidates have 5+ years in quota-carrying enterprise sales and can clearly explain why a sales deliverable

Qualifications

• 5+ years of quota-carrying B2B sales experience.
• Experience as Account Executive or SDR selling to enterprise organizations.
• Strong written communication and ability to explain why a sales deliverable resonates with buyers.

Responsibilities

• Design precise, task-specific grading criteria for a wide range of B2B sales deliverables, including prospecting sequences, discovery call plans, account/territory plans, sales proposals, mutual action plans, and pipeline reviews.
• Evaluate AI-generated and human-created work against established rubrics, providing detailed written justifications for every score.
• Apply objective, consistent, and evidence-based judgment to ensure evaluations are accurate, reproducible, and defensible.
• Incorporate structured feedback from senior reviewers and continuously refine evaluation quality.

Job description

Weekday 1 is seeking experienced sales professionals to join an AI evaluation initiative that improves how next-generation AI systems understand and perform real-world B2B sales work. You will define evaluation criteria and structured rubrics instead of producing sales outputs.

This remote, independent contractor role offers $100-$150 per hour with flexible hours and weekly payments. Ideal candidates have 5+ years in quota-carrying enterprise sales and can clearly explain why a sales deliverable