B2B Sales Expert at Weekday AI — Remote

This role is for one of our clients

Compensation: $100-$150 per hour

Join an advanced AI evaluation initiative focused on improving how next-generation AI systems understand and perform real-world B2B sales work. We are seeking experienced sales professionals to help establish the standard for high-quality sales execution by designing evaluation criteria and assessing AI-generated and human-created sales deliverables.

Rather than creating sales deliverables yourself, you will define what exceptional work looks like by developing structured grading frameworks and providing thoughtful, evidence-based evaluations.

Requirements

### Key Responsibilities

• Design precise, task-specific grading criteria for a wide range of B2B sales deliverables, including:
• Prospecting sequences and outreach emails
• Discovery and demo call plans
• Account and territory plans
• Sales proposals
• Mutual action plans
• Pipeline reviews and sales forecasting
• 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.

### Core Qualifications

• 5+ years of professional B2B sales experience in quota-carrying roles.
• Proven experience as an Account Executive, Sales Development Representative (SDR), or similar client-facing sales role selling to enterprise organizations.
• Strong expertise across the full B2B sales lifecycle, including:
• Outbound prospecting and sequencing
• Discovery and qualification
• Multi-stakeholder enterprise sales
• Pipeline management and forecasting
• Structured sales methodologies
• Exceptional written communication skills with the ability to clearly explain why a sales deliverable would—or would not—resonate with a prospective buyer.
• Strong attention to detail and the ability to apply evaluation criteria consistently across large volumes of work.

### Preferred Qualifications

• Experience evaluating AI-generated content, participating in AI training projects, or working on human evaluation and data annotation initiatives.
• Experience developing, reviewing, or applying structured scoring rubrics.
• Ability to provide constructive, well-reasoned feedback while maintaining high evaluation standards.

### Application Process

• Submit your resume or relevant professional background for consideration.
• Qualified applicants may be invited to complete a brief assessment or provide additional information as part of the selection process.

### Equal Opportunity

We are committed to creating an inclusive environment where all qualified applicants receive equal consideration. Reasonable accommodations are available throughout the application and engagement process upon request.

### Contract & Payment Terms

• Independent contractor engagement.
• Fully remote with flexible working hours.
• Projects may be extended, shortened, or concluded based on business needs and performance.
• Weekly payments are processed through supported payment platforms.
• Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity.