B2B Sales Expert

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Weekday (YC W21)

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2021

💼 Consulting

👥 HR Tech

☁️ SaaS

Consulting • HR Tech • SaaS

Weekday is a modern recruitment platform that combines AI technologies with a vast database of potential candidates, aiming to streamline the hiring process for companies in India. They offer various services, including a proactive outreach approach that helps employers connect with top talent, as well as tools for candidates to easily apply for jobs. Weekday's emphasis on candidate engagement through multiple channels, including email, WhatsApp, and phone calls, sets it apart in the competitive landscape of recruitment agencies.

📋 Description

• Join an advanced AI evaluation initiative focused on improving how next-generation AI systems understand and perform real-world B2B sales work. • Help establish the standard for high-quality sales execution by designing evaluation criteria and assessing AI-generated and human-created sales deliverables. • Define what exceptional work looks like by developing structured grading frameworks and providing thoughtful, evidence-based evaluations. • 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.

🎯 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. • Experience evaluating AI-generated content, participating in AI training projects, or working on human evaluation and data annotation initiatives (preferred). • Experience developing, reviewing, or applying structured scoring rubrics (preferred).