Senior B2B Sales Evaluator (Remote)

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

Benefits offered by this job

Fully remote work

Weekly payments

Job summary

Weekday AI is seeking experienced B2B sales professionals to join an advanced AI evaluation initiative. The role focuses on designing evaluation criteria and grading rubrics for AI-generated and human-created sales deliverables rather than producing deliverables.

This independent contractor position is fully remote in the United States, with weekly payments and flexible hours. Candidates should have 5+ years in quota-carrying roles and strong written communication to justify scores.

Qualifications

• 5+ years of professional B2B sales experience in quota-carrying roles.
• Experience as Account Executive, SDR, or similar client-facing role selling to enterprise organizations.
• Strong expertise across outbound prospecting, discovery, qualification, multi-stakeholder enterprise sales, pipeline management, forecasting, and structured sales methodologies.
• Exceptional written communication skills with the ability to justify scores and conclusions clearly.
• Strong attention to detail and ability to apply evaluation criteria consistently across large volumes of work.

Responsibilities

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

Skills

B2B sales experience

Account Executive; SDR

Sales lifecycle mastery

Written communication

Attention to detail

Job description

Weekday AI is seeking experienced B2B sales professionals to join an advanced AI evaluation initiative. The role focuses on designing evaluation criteria and grading rubrics for AI-generated and human-created sales deliverables rather than producing deliverables.

This independent contractor position is fully remote in the United States, with weekly payments and flexible hours. Candidates should have 5+ years in quota-carrying roles and strong written communication to justify scores.