[Hiring] B2B Sales Expert @Weekday AI

Role Description

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.

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.

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.