Weekday AI (YC W21)

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
<ul>
<li>Design precise, task-specific grading criteria for a wide range of B2B sales deliverables, including:
</li>
<li>Prospecting sequences and outreach emails
</li>
<li>Discovery and demo call plans
</li>
<li>Account and territory plans
</li>
<li>Sales proposals
</li>
<li>Mutual action plans
</li>
<li>Pipeline reviews and sales forecasting
</li>
<li>Evaluate AI-generated and human-created work against established rubrics, providing detailed written justifications for every score
</li>
<li>Apply objective, consistent, and evidence-based judgment to ensure evaluations are accurate, reproducible, and defensible
</li>
<li>Incorporate structured feedback from senior reviewers and continuously refine evaluation quality
</li>
</ul>
Core Qualifications
<ul>
<li>5+ years of professional B2B sales experience in quota-carrying roles
</li>
<li>Proven experience as an Account Executive, Sales Development Representative (SDR), or similar client-facing sales role selling to enterprise organizations
</li>
<li>Strong expertise across the full B2B sales lifecycle, including:
</li>
<li>Outbound prospecting and sequencing
</li>
<li>Discovery and qualification
</li>
<li>Multi-stakeholder enterprise sales
</li>
<li>Pipeline management and forecasting
</li>
<li>Structured sales methodologies
</li>
<li>Exceptional written communication skills with the ability to clearly explain why a sales deliverable would—or would not—resonate with a prospective buyer
</li>
<li>Strong attention to detail and the ability to apply evaluation criteria consistently across large volumes of work
</li>
</ul>
Preferred Qualifications
<ul>
<li>Experience evaluating AI-generated content, participating in AI training projects, or working on human evaluation and data annotation initiatives</li>
<li>Experience developing, reviewing, or applying structured scoring rubrics</li>
<li>Ability to provide constructive, well-reasoned feedback while maintaining high evaluation standards</li>
</ul>
Application Process
<ul>
<li>Submit your resume or relevant professional background for consideration</li>
<li>Qualified applicants may be invited to complete a brief assessment or provide additional information as part of the selection process</li>
</ul>
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 &amp; Payment Terms
<ul>
<li>Independent contractor engagement</li>
<li>Fully remote with flexible working hours</li>
<li>Projects may be extended, shortened, or concluded based on business needs and performance</li>
<li>Weekly payments are processed through supported payment platforms</li>
<li>Applicants requiring H-1B or STEM OPT sponsorship are not eligible for this opportunity</li>
</ul>

B2B Sales Expert

B2B Sales Expert

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