B2B Sales Expert
Weekday AI
•$100 - $150•Remote
About The Position
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
- 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.
Nice To Haves
- 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.
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.
Benefits
- Weekly payments are processed through supported payment platforms.
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What This Job Offers
Career Level
Senior
Education Level
No Education Listed
